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Ethyl 3,4-bis(2-methoxyethoxy)benzoate is an organic compound that serves as a key intermediate in the synthesis of various pharmaceuticals, particularly in the production of cancer treatment medicines.

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  • 183322-16-9 Structure
  • Basic information

    1. Product Name: Ethyl 3,4-bis(2-methoxyethoxy)benzoate
    2. Synonyms: 3,4-Bis(2-methoxyethoxy)benzoic acid ethyl ester;Ethyl 3,4-bis(2-methoxyethoxy)benzoate;Thyl3,4-bis(2-methoxyethoxy)benzoate;Erlotinib interMediate II;Benzoic acid,3,4-bis(2-Methoxyethoxy)-, ethyl ester;183322-16-9;3,4-bis(2-methoxyethoxy)benzoate;Ethyl 3,4-bis(2-methoxyethoxy)
    3. CAS NO:183322-16-9
    4. Molecular Formula: C15H22O6
    5. Molecular Weight: 298.33158
    6. EINECS: 1312995-182-4
    7. Product Categories: Erlotinib
    8. Mol File: 183322-16-9.mol
    9. Article Data: 22
  • Chemical Properties

    1. Melting Point: 55-58 °C
    2. Boiling Point: 401.7 °C at 760 mmHg
    3. Flash Point: 175.5 °C
    4. Appearance: /
    5. Density: 1.102
    6. Vapor Pressure: 1.15E-06mmHg at 25°C
    7. Refractive Index: 1.488
    8. Storage Temp.: Sealed in dry,Room Temperature
    9. Solubility: N/A
    10. CAS DataBase Reference: Ethyl 3,4-bis(2-methoxyethoxy)benzoate(CAS DataBase Reference)
    11. NIST Chemistry Reference: Ethyl 3,4-bis(2-methoxyethoxy)benzoate(183322-16-9)
    12. EPA Substance Registry System: Ethyl 3,4-bis(2-methoxyethoxy)benzoate(183322-16-9)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 183322-16-9(Hazardous Substances Data)

183322-16-9 Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 3,4-bis(2-methoxyethoxy)benzoate is used as a key intermediate in the synthesis of Erlotinib (E625008), a cancer treatment medicine. It plays a crucial role in the development of this medication, which is designed to target and inhibit the epidermal growth factor receptor (EGFR), thereby helping to control the growth and spread of cancer cells.

Check Digit Verification of cas no

The CAS Registry Mumber 183322-16-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,8,3,3,2 and 2 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 183322-16:
(8*1)+(7*8)+(6*3)+(5*3)+(4*2)+(3*2)+(2*1)+(1*6)=119
119 % 10 = 9
So 183322-16-9 is a valid CAS Registry Number.
InChI:InChI=1/C15H22O6/c1-4-19-15(16)12-5-6-13(20-9-7-17-2)14(11-12)21-10-8-18-3/h5-6,11H,4,7-10H2,1-3H3

183322-16-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl 3,4-bis(2-methoxyethoxy)benzoate

1.2 Other means of identification

Product number -
Other names Ethyl 3,4-bis(2-methoxyethoxy)benzoate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:183322-16-9 SDS

183322-16-9Synthetic route

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

2-Bromoethyl methyl ether
6482-24-2

2-Bromoethyl methyl ether

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetone at 60℃; for 19h; Inert atmosphere;100%
With potassium carbonate In acetone at 20 - 70℃; for 24h;93%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone for 64h; Inert atmosphere; Reflux;93%
3,4-bis(2-methoxyethoxy)-benzoic acid
819813-71-3

3,4-bis(2-methoxyethoxy)-benzoic acid

ethanol
64-17-5

ethanol

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions
ConditionsYield
With sulfuric acid Cooling with ice; Reflux;98%
2-chloroethyl methyl ether
627-42-9

2-chloroethyl methyl ether

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions
ConditionsYield
With 4-(Methylamino)pyridine; potassium carbonate at 90 - 95℃; Temperature; Reagent/catalyst;95%
With carbon dioxide; ammonia at 50℃; for 0.5h; Temperature; Reagent/catalyst;94.6%
With potassium tert-butylate; potassium iodide In N,N-dimethyl-formamide at 100℃; for 12h;87%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone for 120h; Heating;
With potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; for 9h;95 %Chromat.
2-methoxyethyl methanesulfonate
16427-44-4

2-methoxyethyl methanesulfonate

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In toluene for 6h; Reflux;95%
With potassium tert-butylate; tetrabutylammomium bromide In N,N-dimethyl-formamide at 30 - 40℃; for 10h;90.5%
Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

2-methoxy-ethyl p-toluenesulfonyloxy ester
17178-10-8

2-methoxy-ethyl p-toluenesulfonyloxy ester

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 6h; Reflux;89%
With potassium carbonate In acetonitrile for 6h; Reflux;89%
4-chloro-6,7-di-(2-methoxyethoxy)quinazoline hydrochloride

4-chloro-6,7-di-(2-methoxyethoxy)quinazoline hydrochloride

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

2-Bromoethyl methyl ether
6482-24-2

2-Bromoethyl methyl ether

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / 10 h / 40 - 80 °C
2: potassium tert-butylate; potassium iodide / N,N-dimethyl-formamide / 12 h / 100 °C
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester
179688-26-7

2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions
ConditionsYield
With sulfuric acid; nitric acid In acetic acid at 20 - 70℃; for 2h;100%
With sulfuric acid; nitric acid In acetic acid at 15 - 35℃;100%
With sulfuric acid; nitric acid; acetic anhydride; acetic acid at 40℃; for 2h; Concentration; Large scale;98.3%
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

C15H22O7

C15H22O7

Conditions
ConditionsYield
Stage #1: 3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester In tetrahydrofuran for 0.5h; Reflux;
Stage #2: With peracetic acid; dinitrogen monoxide In tetrahydrofuran at 50℃; under 22502.3 Torr; for 2h; Reagent/catalyst; Temperature; Autoclave;
95.2%
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

3,4-bis(2-methoxyethoxy)-benzoic acid
819813-71-3

3,4-bis(2-methoxyethoxy)-benzoic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water at 20℃; for 3h;90%
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one
179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid; nitric acid / 24 h / 20 °C
2: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr
3: 84 percent / 12 h / 165 - 170 °C
View Scheme
Multi-step reaction with 3 steps
1: nitric acid; trifluoroacetic acid / CH2Cl2 / 20 °C
2: 94 percent / hydrogen / palladium on activated carbon / methanol
3: 62 percent / formamide / 3 h / 160 °C
View Scheme
Multi-step reaction with 3 steps
1: acetic acid; nitric acid / 0 °C
2: hydrogen; palladium on activated charcoal / methanol
3: 165 - 170 °C
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

4-chloro-6,7-bis(2-methoxyethoxy)quinazoline
183322-18-1

4-chloro-6,7-bis(2-methoxyethoxy)quinazoline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid; nitric acid / 24 h / 20 °C
2: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr
3: 84 percent / 12 h / 165 - 170 °C
4: phosphoryl choride; N,N-diethylaniline / 0.67 h / 70 - 90 °C
View Scheme
Multi-step reaction with 4 steps
1: nitric acid; trifluoroacetic acid / CH2Cl2 / 20 °C
2: 94 percent / hydrogen / palladium on activated carbon / methanol
3: 62 percent / formamide / 3 h / 160 °C
4: 98 percent / oxalyl chloride / CHCl3; dimethylformamide / 1.5 h / Heating
View Scheme
Multi-step reaction with 3 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: acetic acid; nitric acid / 24 h / 20 °C
2: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr
3: 84 percent / 12 h / 165 - 170 °C
4: phosphoryl choride; N,N-diethylaniline / 0.67 h / 70 - 90 °C
5: pyridine / propan-2-ol
View Scheme
Multi-step reaction with 6 steps
1.1: sulfuric acid; nitric acid / 1 h / 20 °C / Darkness
2.1: palladium 10% on activated carbon / ethanol / 10 h / 20 °C
2.2: 20 °C
3.1: ammonium formate; triethylamine / 6 h / 160 °C
4.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 50 °C
5.1: methanol / 3 h / 20 - 30 °C
5.2: 3 h / 50 °C
6.1: hydrogenchloride / water; dichloromethane; methanol / 3 h / 25 °C
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate
179688-27-8

ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; nitric acid / 24 h / 20 °C
2: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr
View Scheme
Multi-step reaction with 2 steps
1: nitric acid; trifluoroacetic acid / CH2Cl2 / 20 °C
2: 94 percent / hydrogen / palladium on activated carbon / methanol
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid; nitric acid / acetic acid / 15 - 35 °C
2: hydrogen; platinum on carbon / methanol / 20 - 40 °C / 760.05 Torr
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

4-(3'-chloro-4'-fluoroanilino)-6,7-bis(2-methoxyethoxy)-quinazoline

4-(3'-chloro-4'-fluoroanilino)-6,7-bis(2-methoxyethoxy)-quinazoline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: nitric acid; trifluoroacetic acid / CH2Cl2 / 20 °C
2: 94 percent / hydrogen / palladium on activated carbon / methanol
3: 62 percent / formamide / 3 h / 160 °C
4: 98 percent / oxalyl chloride / CHCl3; dimethylformamide / 1.5 h / Heating
5: 53 percent / pyridine / propan-2-ol / 2 h / Heating
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

6,7-bis(2-methoxyethoxy)quinazolin-4(3H)-one
179688-29-0

6,7-bis(2-methoxyethoxy)quinazolin-4(3H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
View Scheme
Multi-step reaction with 2 steps
1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice
2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sulfuric acid; nitric acid / acetic acid / 15 - 35 °C
2.1: hydrogen; platinum on carbon / methanol / 20 - 40 °C / 760.05 Torr
3.1: N,N-dimethyl-formamide / 10 h / 130 - 140 °C
3.2: 65 - 80 °C
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

9-chloro-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline
1347720-71-1

9-chloro-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: isopropyl alcohol / 4 h / Reflux
5.1: trichlorophosphate / 2 h / Reflux
5.2: pH 10
View Scheme
Multi-step reaction with 5 steps
1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice
2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C
3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
4: isopropyl alcohol / 4 h / Reflux
5: trichlorophosphate / 2 h / Reflux
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

9-bromo-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline
1347720-74-4

9-bromo-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: pyridine / acetonitrile / 4 h / Reflux
5.1: trichlorophosphate / 2 h / Reflux
5.2: pH 9
View Scheme
Multi-step reaction with 5 steps
1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice
2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C
3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
4: pyridine / acetonitrile / 4 h / Reflux
5: trichlorophosphate / 2 h / Reflux
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

9-fluoro-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline
1347719-30-5

9-fluoro-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: hydrogenchloride / isopropyl alcohol; water
5.1: triethylamine; methanesulfonyl chloride / toluene / 7 h / 20 °C / cooling with ice
View Scheme
Multi-step reaction with 5 steps
1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice
2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C
3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
4: hydrogenchloride / isopropyl alcohol; water / 20 °C
5: triethylamine; methanesulfonyl chloride / toluene / 7 h / 20 °C / Cooling with ice
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

9-ethynyl-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline
1347720-79-9

9-ethynyl-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: pyridine / acetonitrile / 4 h / Reflux
5.1: trichlorophosphate / 2 h / Reflux
5.2: pH 9
6.1: hydrogenchloride / ethanol; water / Heating
7.1: triethylamine / triphenylphosphine; palladium diacetate; copper(l) iodide / 7 h / Inert atmosphere; Reflux
8.1: sodium hydroxide / toluene / 6 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 8 steps
1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice
2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C
3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
4: pyridine / acetonitrile / 4 h / Reflux
5: trichlorophosphate / 2 h / Reflux
6: hydrogenchloride / ethanol / Heating
7: triethylamine; triphenylphosphine; palladium diacetate; copper(l) iodide / 7 h / Inert atmosphere; Reflux
8: sodium hydroxide / toluene / 4 h / Resolution of racemate; Inert atmosphere
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

9-nitro-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline
1347719-34-9

9-nitro-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: hydrogenchloride / 1,4-dioxane; water / 7 h / 20 °C
5.1: triethylamine; methanesulfonyl chloride / chloroform / 20 °C / cooling with ice
View Scheme
Multi-step reaction with 5 steps
1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice
2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C
3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
4: hydrogenchloride / water; 1,4-dioxane / 7 h / 20 °C
5: triethylamine; methanesulfonyl chloride / chloroform / 20 °C
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

9-amino-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline
1347720-84-6

9-amino-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: hydrogenchloride / 1,4-dioxane; water / 7 h / 20 °C
5.1: triethylamine; methanesulfonyl chloride / chloroform / 20 °C / cooling with ice
6.1: hydrogen / palladium 10% on activated carbon / methanol / 5 h / 760.05 Torr / Reflux
View Scheme
Multi-step reaction with 6 steps
1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice
2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C
3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
4: hydrogenchloride / water; 1,4-dioxane / 7 h / 20 °C
5: triethylamine; methanesulfonyl chloride / chloroform / 20 °C
6: hydrogen; palladium 10% on activated carbon / methanol / 5 h / 760.05 Torr / Reflux
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

9-chloro-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline hydrochloride

9-chloro-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: isopropyl alcohol / 4 h / Reflux
5.1: trichlorophosphate / 2 h / Reflux
5.2: pH 10
6.1: hydrogenchloride / ethanol; water / Heating
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

9-fluoro-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline mesylate

9-fluoro-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline mesylate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: hydrogenchloride / isopropyl alcohol; water
5.1: triethylamine; methanesulfonyl chloride / toluene / 7 h / 20 °C / cooling with ice
6.1: ethanol / 0.5 h / Reflux
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

9-ethynyl-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline hydrochloride

9-ethynyl-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: pyridine / acetonitrile / 4 h / Reflux
5.1: trichlorophosphate / 2 h / Reflux
5.2: pH 9
6.1: hydrogenchloride / ethanol; water / Heating
7.1: triethylamine / triphenylphosphine; palladium diacetate; copper(l) iodide / 7 h / Inert atmosphere; Reflux
8.1: sodium hydroxide / toluene / 6 h / Inert atmosphere; Reflux
9.1: hydrogenchloride / ethanol
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

9-amino-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline hydrobromide

9-amino-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline hydrobromide

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: hydrogenchloride / 1,4-dioxane; water / 7 h / 20 °C
5.1: triethylamine; methanesulfonyl chloride / chloroform / 20 °C / cooling with ice
6.1: hydrogen / palladium 10% on activated carbon / methanol / 5 h / 760.05 Torr / Reflux
7.1: hydrogen bromide / ethyl acetate; ethanol
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

C21H24ClN3O5
1347720-70-0

C21H24ClN3O5

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: isopropyl alcohol / 4 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice
2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C
3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
4: isopropyl alcohol / 4 h / Reflux
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

C21H24BrN3O5
1347720-73-3

C21H24BrN3O5

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: pyridine / acetonitrile / 4 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice
2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C
3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
4: pyridine / acetonitrile / 4 h / Reflux
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

9-bromo-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline hydrochloride

9-bromo-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: pyridine / acetonitrile / 4 h / Reflux
5.1: trichlorophosphate / 2 h / Reflux
5.2: pH 9
6.1: hydrogenchloride / ethanol; water / Heating
View Scheme
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

C21H24FN3O5
1347720-76-6

C21H24FN3O5

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: hydrogenchloride / isopropyl alcohol; water
View Scheme
Multi-step reaction with 4 steps
1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice
2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C
3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
4: hydrogenchloride / isopropyl alcohol; water / 20 °C
View Scheme

183322-16-9Relevant articles and documents

Synthetic method of erlotinib

-

Paragraph 0040-0042; 0043-0044, (2020/07/12)

The invention relates to a synthetic method of erlotinib, and belongs to the technical field of chemical synthesis. The preparation method comprises the following synthesis steps: (1) reacting a compound I with 2-chloroethyl methyl ether to generate a compound II; (2) oxidizing the compound II through peracetic acid to generate a compound III; (3) reacting the compound III with benzene sulfonyl chloride to generate a compound IV; (4) carrying out a ring closing reaction on the compound IV, ammonium chloride and formamide to generate a compound V; (5) reacting the compound V with phosphorus oxychloride to generate a compound VI; and (6) reacting the compound VI with m-aminophenylacetylene to generate a compound VII erlotinib. The invention provides a new synthetic route, and the used raw materials are common materials, are simple and easily available, can adapt to production of various scales, and the synthetic method has good industrial production prospects.

Synthesis and evaluation of novel 18F-labeled quinazoline derivatives with low lipophilicity for tumor PET imaging

Chong, Yan,Chang, Jin,Zhao, Wenwen,He, Yong,Li, Yuqiao,Zhang, Huabei,Qi, Chuanmin

, p. 42 - 53 (2018/02/06)

Four novel 18F-labeled quinazoline derivatives with low lipophilicity, [18F]4-(2-fluoroethoxy)-6,7-dimethoxyquinazoline ([18F]I), [18F]4-(3-((4-(2-fluoroethoxy)-7-methoxyquinazolin-6-yl)oxy)propyl)morpholine ([18F]II), [18F]4-(2-fluoroethoxy)-7-methoxy-6-(2-methoxyethoxy)quinazoline ([18F]III), and [18F]4-(2-fluoroethoxy)-6,7-bis(2-methoxyethoxy)quinazoline ([18F]IV), were synthesized via a 2-step radiosynthesis procedure with an overall radiochemical yield of 10% to 38% (without decay correction) and radiochemical purities of >98%. The lipophilicity and stability of labeled compounds were tested in vitro. The log P values of the 4 radiotracers ranged from 0.52 to 1.07. We then performed ELISA to measure their affinities to EGFR-TK; ELISA assay results indicated that each inhibitor was specifically bounded to EGFR-TK in a dose-dependent manner. The EGFR-TK autophosphorylation IC50 values of [18F]I, [18F]II, [18F]III, and [18F]IV were 7.732, 0.4698, 0.1174, and 0.1176?μM, respectively. All labeled compounds were evaluated via cellular uptake and blocking studies in HepG2 cell lines in vitro. Cellular uptake and blocking experiment results indicated that [18F]I and [18F]III had excellent cellular uptake at 120-minute postinjection in HepG2 carcinoma cells (51.80?±?3.42%ID/mg protein and 27.31?±?1.94%ID/mg protein, respectively). Additionally, biodistribution experiments in S180 tumor-bearing mice in vivo indicated that [18F]I had a very fast clearance in blood and a relatively high uptake ratio of tumor to blood (4.76) and tumor to muscle (1.82) at 60-minute postinjection. [18F]III had a quick clearance in plasma, and its highest uptake ratio of tumor to muscle was 2.55 at 15-minute postinjection. These experimental results and experiences were valuable for the further exploration of novel radiotracers of quinazoline derivatives.

A method for preparing environmental protection of erlotinib hydrochloride

-

, (2017/09/26)

The invention discloses an environment-friendly method for preparing high-yield erlotinib hydrochloride. The method comprises the following steps: directly performing cyclic condensation by taking 2-amino-4,5-di(2-methoxy ethyoxyl) ethyl benzoate hydrochloride as a key intermediate, reacting with aminophenylacetylene to generate erlotinib hydrochloride after performing chlorination, and refining to obtain the high-purity erlotinib hydrochloride. The process route provided by the invention is mild in reaction condition and high in yield; the first-class reagent and other reagents harmful to the environment and the operators are not used, the byproduct is few, the aftertreatment is simple and the commercial process can be easily processed.

Preparation method of 3,4-di(2-methoxyl ethoxyl) ethyl benzoate

-

Paragraph 0029; 0030, (2017/07/19)

The invention belongs to the field of drug synthesis and relates to a preparation method of an anticancer drug intermediate, and in particular to a preparation method of 3,4-di(2-methoxyl ethoxyl) ethyl benzoate. The formula is as shown in the description. The preparation method is researched and reported in many literatures or patents, but organic solvents such as acetonitrile, acetone and DMF are needed to take part in. According to the preparation method provided by the invention, the solvents in the existing literatures or patents are not needed, but a product which is high in yield and purity can be obtained. The preparation method is a green and environmental-friendly preparation method and is suitable for industrial production.

Erlotinid hydrochloride method for the preparation of key intermediate

-

Paragraph 0058; 0059, (2016/11/09)

The invention discloses a preparation method of an erlotinib hydrochloride key intermediate 4-chloro-6,7-di(2-methoxyethoxy)quinazoline, which comprises the following steps: reacting the raw material ethyl 3,4-dihydroxybenzoate with ethyl 2-methoxysulfonate, nitrating, reducing, cyclizing and chlorinating to obtain the key intermediate 4-chloro-6,7-di(2-methoxyethoxy)quinazoline. The method has the advantages of mild reaction conditions, low cost, high purity and high total yield (up to 74.8%), and can easily implement industrial production.

Model quinazoline chlorethazine compound and its preparation method and application for treating tumor (by machine translation)

-

Paragraph 0106; 0107; 0108, (2016/10/07)

A novel quinazoline nitrogen mustard compound is characterized in that: one end is provided with a nitrogen mustard alkylating group; the other end is provided with a 6, 7-substituted quinazoline structure; a substituent R1 is located at a site 4 of a quinazoline matrix, and represents 2-, 3-, 4- nitrogen mustard substituent; and substituents R2, R3 are located at site 6 and 7 of a quinazoline matrix, and represent methoxyethoxy, methoxy, morpholine propoxy, 3-etrahydrofuran oxygen group and hydroxyl group. The compound has a structure shown as a formula A. Experiments show that the compound can cause cross-linking of DNA, and is a bifunctional alkylating agent. In vivo antitumor activity experiment show that the compound has good activity; furthermore, the compound has the advantage of low toxicity, which a nitrogen mustard drug is lack of. At the same time, the compound is easy for synthesis, has high total yield. Advantages of the compound show that it has great potential to become a drug for treatment of cancer.

Quinazoline derivatives

-

Paragraph 0125, (2016/08/23)

no abstract published

A Mild and Regioselective Route to Functionalized Quinazolines

Maiden, Tracy M. M.,Swanson, Stephen,Procopiou, Panayiotis A.,Harrity, Joseph P. A.

supporting information, p. 14342 - 14346 (2015/10/05)

A Rh-catalyzed ortho-amidation cyclocondensation sequence gave a range of 4-aminoquinazolines in high yield. The method features a remarkably mild C(sp2)-H activation step and can be exploited to rapidly access compounds with established biological activity.

Isolation of highly pure erlotinib hydrochloride by recrystallization after nucleophilic substitution of an impurity with piperazine

Zhang, Gengzhen,Zha, Linlin

, p. 2303 - 2309 (2013/07/26)

Optimized synthesis and purification of erlotinib hydrochloride (N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazoline-4-amine hydrochloride) were studied. Highly polar piperazine was used in a nucleophilic substitution reaction with the chlorinated intermediate byproduct N-(3-ethynylphenyl)-6(2- chloroethoxy)-7-(2-methoxyethoxy)quinazolin-4-amine hydrochloride. As a result, N-(3-ethynylphenyl)-6(2-chloroethoxy)-7-(2-methoxyethoxy)quinazolin-4-amine hydrochloride was completely transformed to N-(3-ethynylphenyl)-6(2- piperzinoethoxy)-7-(2-methoxyethoxy)quinazolin-4-amine hydrochloride. The polarity of N-(3-ethynylphenyl)-6(2-piperzinoethoxy)-7-(2-methoxyethoxy) quinazolin-4-amine hydrochloride was changed, and its molecule was enlarged. It was easy to remove this larger, more polar, compound by recrystallization. Highly pure erlotinib hydrochloride was obtained with low impurity content (99.9 %.

FUSED QUINAZOLINE DERIVATIVES AND USES THEREOF

-

Paragraph 0258, (2013/05/23)

Fused quinazoline derivatives and uses thereof as protein tyrosine kinase inhibitors and aurora kinase inhibitors are disclosed. Said protein tyrosine kinase inhibitors and aurora kinase inhibitors can be used in treating cancers, leukaemia and the diseases relevant to differentiation and proliferation. Said protein tyrosine kinase and aurora kinase dual inhibitors are the compounds represented by the following general formula or salts thereof.

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