Ethyl 4-acetoxy-2-(ethylthio)-6,7-difluoroquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 4-acetoxy-2-(ethylthio)-6,7-difluoroquinoline-3-carboxylate
• CAS No.: 154330-68-4
• Molecular Formula: C₁₆H₁₅F₂NO₄S
• Molecular Weight: 355.362
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID50444551
• Nikkaji Number: J920.591H
• Wikidata: Q72472164
• Mol file: 154330-68-4.mol

Synonyms:154330-68-4;Ethyl 4-acetoxy-2-(ethylthio)-6,7-difluoroquinoline-3-carboxylate;Ethyl 4-acetoxy-6,7-difluoro-2-(ethylthio)quinoline-3-carboxylate;ethyl 4-acetyloxy-2-ethylsulfanyl-6,7-difluoroquinoline-3-carboxylate;SCHEMBL4089333;DTXSID50444551;(ethylthio)quinoline-3-carboxylate;BCP13620;ethyl 4-acetoxy-2-ethylsulfanyl-6,7-difluoro-quinoline-3-carboxylate;AKOS015897398;AC-2014;SB72612;CS-0447356;FT-0652832;A809526;Q-101930;Ethyl4-acetoxy-2-(ethylthio)-6,7-difluoroquinoline-3-carboxylate;Ethyl4-acetoxy-6,7-difluoro-2-(ethylthio)quinoline-3-carboxylate;4-Acetoxy-2-ethylthio-6,7-difluoro-3-quinolinecarboxylic acid ethyl ester;ethyl 4-(acetyloxy)-2-(ethylsulfanyl)-6,7-difluoroquinoline-3-carboxylate;4-(acetyloxy)-2-(ethylthio)-6,7-difluoro-3-quinolinecarboxylic acid ethyl ester

Chemical Property of Ethyl 4-acetoxy-2-(ethylthio)-6,7-difluoroquinoline-3-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.579
• Boiling Point: 442.971 °C at 760 mmHg
• PKA: -1.18±0.61(Predicted)
• Flash Point: 221.701 °C
• PSA: 90.79000
• Density: 1.367 g/cm³
• LogP: 3.72700
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 355.06898546
• Heavy Atom Count: 24
• Complexity: 467

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 4-acetoxy-2-(ethylthio)-6,7-difluoroquinoline-3-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C2=CC(=C(C=C2N=C1SCC)F)F)OC(=O)C

Technology Process of Ethyl 4-acetoxy-2-(ethylthio)-6,7-difluoroquinoline-3-carboxylate

There total 9 articles about Ethyl 4-acetoxy-2-(ethylthio)-6,7-difluoroquinoline-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

acetyl chloride (75-36-5) + ethyl 4-hydroxy-6,7-difluoro-2-(ethylthio)quinoline-3-carboxylate (849744-52-1,154330-67-3) → ethyl 4-acetoxy-6,7-difluoro-2-(ethylthio)quinoline-3-carboxylate (154330-68-4)

Guidance literature:

With triethylamine; In chloroform; at 0 ℃; for 1h;

DOI:10.1002/jhet.5570340622

Reference yield:

diethyl[bis(ethylsulfanyl)methylene]malonate (55084-17-8) → ethyl 4-acetoxy-6,7-difluoro-2-(ethylthio)quinoline-3-carboxylate (154330-68-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / m-CPBA / CH₂Cl₂ / 4 h / Ambient temperature

2: 67 percent / 48 h / 70 °C

3: 79 percent / xylene / 3 h / Heating

4: 93 percent / Et₃N / CHCl₃ / 1 h / 0 °C

With triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; chloroform; xylene;

DOI:10.1002/jhet.5570340622

Reference yield:

ethyl 2,4,5-trifluorobenzoylacetate (98349-24-7) → ethyl 4-acetoxy-6,7-difluoro-2-(ethylthio)quinoline-3-carboxylate (154330-68-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) K₂CO₃ / 1.) DMF, 0 deg C, 5 min, 2.) DMF, 0 deg C, 3 h

2: 53 percent / NH₃ / ethanol / 18 h / 80 °C

3: 58 percent / KHCO₃ / dimethylformamide / 24 h / 80 °C

4: 93 percent / Et₃N / CHCl₃ / 1 h / 0 °C

With ammonia; potassium carbonate; potassium hydrogencarbonate; triethylamine; In ethanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570340622

upstream raw materials:

acetyl chloride

ethyl 4-hydroxy-6,7-difluoro-2-(ethylthio)quinoline-3-carboxylate

diethyl[bis(ethylsulfanyl)methylene]malonate

ethyl 2,4,5-trifluorobenzoylacetate

Downstream raw materials:

ethyl 6,7-difluoro-1-methyl-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate

Refernces

• 1、 Matsuoka,Segawa,Makita,Ohmachi,Kashima,Nakamura K.-,Hattori,Kitano,Kise. "Studies on pyridonecarboxylic acids. V. A practical synthesis of ethyl 6,7-difluoro-1-methyl-4-oxo-4H-[1,3]thiazeto[3,2-α]quinoline 3-carboxylate, a key intermediate for the new tricyclic quinolone, prulifloxacin (nm441) and versatile new syntheses of the 2-thioquinoline skeleton". . p. 1773 - 1779. Retrieved 2007/10/03.