6-Amino-3,3-dimethylindolin-2-one

Base Information

• Chemical Name: 6-Amino-3,3-dimethylindolin-2-one
• CAS No.: 100510-65-4
• Molecular Formula: C10H12N2O
• Molecular Weight: 176.218
• Hs Code.: 2933790090
• DSSTox Substance ID: DTXSID40544514
• Wikidata: Q82421630
• Mol file: 100510-65-4.mol

Synonyms:6-Amino-3,3-dimethylindolin-2-one;100510-65-4;6-AMINO-3,3-DIMETHYL-1H-INDOL-2-ONE;6-AMINO-3,3-DIMETHYL-2-OXO-1,3-DIHYDRO-INDOLE;2H-Indol-2-one, 6-amino-1,3-dihydro-3,3-dimethyl-;6-Amino-3,3-dimethyl-1,3-dihydro-indol-2-one;MFCD11053509;6-amino-3,3-dimethyl-1,3-dihydro-2h-indol-2-one;SCHEMBL496554;DTXSID40544514;IWARVYFPBLDOAK-UHFFFAOYSA-N;AMY20404;AKOS006308940;AC-3265;CS-W003764;SB15985;DS-13950;SY004726;6-Amino-3 pound not3-dimethylindolin-2-one;6-Amino-3,3-dimethylindolin-2-one, AldrichCPR;A848314

Chemical Property of 6-Amino-3,3-dimethylindolin-2-one

Chemical Property:

• Vapor Pressure: 1.45E-05mmHg at 25°C
• Refractive Index: 1.584
• Boiling Point: 366.6 °C at 760 mmHg
• PKA: 14.32±0.40(Predicted)
• Flash Point: 175.5 °C
• PSA: 55.12000
• Density: 1.161 g/cm³
• LogP: 2.21770
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 176.094963011
• Heavy Atom Count: 13
• Complexity: 237

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-Amino-3,3-dimethylindolin-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2=C(C=C(C=C2)N)NC1=O)C
• Uses: 6-Amino-3,3-dimethylindolin-2-one is a versatile reactant used in the preparation of selective and potent aminoisoquinoline derivatives as inhibitors of mutant B-Raf pathway. It is also used in the synthesis of pentacyclic aurora kinase inhibitors.

Technology Process of 6-Amino-3,3-dimethylindolin-2-one

There total 8 articles about 6-Amino-3,3-dimethylindolin-2-one 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: 87.3%

1,3-Dihydro-3,3-dimethyl-6-nitro-2H-indol-2-one (100510-64-3) → 6-Amino-3,3-dimethylindolin-2-one (100510-65-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; dichloromethane; at 20 ℃;

Reference yield: 64.1%

2-(2,4-dinitro-phenyl)-2-methyl-propionic acid ethyl ester (1256633-16-5) → 6-Amino-3,3-dimethylindolin-2-one (100510-65-4)

Guidance literature:

With iron; ammonium chloride; In ethanol; water; Reflux;

DOI:10.1039/c2md20275a

Reference yield:

ethyl 2-methyl-2-phenylpropionate (2901-13-5) → 6-Amino-3,3-dimethylindolin-2-one (100510-65-4)

Guidance literature:

Multi-step reaction with 2 steps

1: nitric acid; sulfuric acid / 20 °C

2: iron; ammonium chloride / ethanol; water / Reflux

With sulfuric acid; nitric acid; iron; ammonium chloride; In ethanol; water;

DOI:10.1039/c2md20275a

upstream raw materials:

1,3-Dihydro-3,3-dimethyl-6-nitro-2H-indol-2-one

2-(2,4-dinitro-phenyl)-2-methyl-propionic acid ethyl ester

ethyl 2-methyl-2-phenylpropionate

2-methyl-2-phenylpropionic acid

Downstream raw materials:

C₂₆H₂₁FN₄O₃

C₂₄H₂₁N₅O₄

C₂₄H₂₀FN₅O₄

C₂₄H₂₀ClN₅O₄

Refernces

• 1、 -. "2-OXO-2,3-DIHYDRO-INDOLES FOR THE TREATMENT OF CNS DISORDERS". Page/Page column 17. . Retrieved 2014/04/03.
• 2、 Rawson, Thomas E.,Rüth, Matthias,Blackwood, Elizabeth,Burdick, Dan,Corson, Laura,Dotson, Jenna,Drummond, Jason,Fields, Carter,Georges, Guy J.,Goller, Bernhard,Halladay, Jason,Hunsaker, Thomas,Kleinheinz, Tracy,Krell, Hans-Willi,Li, Jun,Liang, Jun,Limberg, Anja,McNutt, Angela,Moffat, John,Phillips, Gail,Ran, Yingqing,Safina, Brian,Ultsch, Mark,Walker, Leslie,Wiesmann, Christian,Zhang, Birong,Zhou, Aihe,Zhu, Bing-Yan,Rüger, Petra,Cochran, Andrea G.. "A pentacyclic aurora kinase inhibitor (AKI-001) with high in vivo potency and oral bioavailability". experimental part. p. 4465 - 4475. Retrieved 2009/07/11.