6-amino-4-trifluoromethylquinolin-2(1H)-one

Base Information

• Chemical Name: 6-amino-4-trifluoromethylquinolin-2(1H)-one
• CAS No.: 328955-57-3
• Molecular Formula: C10H7F3N2O
• Molecular Weight: 228.174
• ChEMBL ID: CHEMBL385509
• DSSTox Substance ID: DTXSID60582115
• Pharos Ligand ID: VTSAX4WF8WML
• Wikidata: Q82473437
• Mol file: 328955-57-3.mol

Synonyms:6-amino-4-trifluoromethylquinolin-2(1H)-one;328955-57-3;6-amino-4-(trifluoromethyl)quinolin-2(1H)-one;6-AMINO-4-(TRIFLUOROMETHYL)-1H-QUINOLIN-2-ONE;2(1H)-Quinolinone, 6-amino-4-(trifluoromethyl)-;6-Amino-4-(trifluoromethyl)-2(1H)-quinolinone;CHEMBL385509;SCHEMBL1770828;SCHEMBL19680530;BDBM18526;DTXSID60582115;AMY42414;MFCD12828493;AKOS015951346;SB69604;AC-27434;PD182822;CS-0084832;6-Amino-4-trifluoromethyl-2(1H)-quinolinone;6-amino-4-trifluoromethyl quinolin-2(1h)-one;G10963;6-AMINO-4-TRIFLUOROMETHYL-QUINOLIN-2-OL;6-Amino-4-(trifluoromethyl)-quinolin-2(1h)-one;6-amino-4-trifluoromethylquinolin-2(1H)-one, 3;J-518230;6-amino-4-(trifluoromethyl)-1,2-dihydroquinolin-2-one

Chemical Property of 6-amino-4-trifluoromethylquinolin-2(1H)-one

Chemical Property:

• PSA: 58.88000
• LogP: 2.71030
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 228.05104734
• Heavy Atom Count: 16
• Complexity: 337

Purity/Quality:

99% ^*data from raw suppliers

6-Amino-4-trifluoromethylquinolin-2(1H)-one 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1N)C(=CC(=O)N2)C(F)(F)F
• Uses: 6-Amino-4-(trifluoromethyl)-2(1H)-quinolinone is an intermediate in the synthesis of LGD-2226 (L397615), an orally active potent and selective androgen receptor modulator used in the treatment of muscle wasting and osteoporosis. Show to have an anabolic effect on muscle and bone tissue.

Technology Process of 6-amino-4-trifluoromethylquinolin-2(1H)-one

There total 6 articles about 6-amino-4-trifluoromethylquinolin-2(1H)-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: 87.0%

6-nitro-4-trifluoromethylquinolin-2(1H)-one (328956-38-3) → 6-amino-4-(trifluoromethyl)quinoline-2-(1H)-one (328955-57-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 96h;

DOI:10.1021/jm060792t

Reference yield:

ethyl 4,4,4-trifluoroacetoacetate (372-31-6) + N-acetyl-p-phenylenediamine (122-80-5) → 6-amino-4-(trifluoromethyl)quinoline-2-(1H)-one (328955-57-3)

Guidance literature:

With sulfuric acid; In diethyl ether; water; ethyl acetate; nitrobenzene;

Reference yield:

4-(trifluoromethyl)quinolin-2(1H)-one (25199-84-2) → 6-amino-4-(trifluoromethyl)quinoline-2-(1H)-one (328955-57-3)

Guidance literature:

Multi-step reaction with 2 steps

1: HNO₃; H₂SO₄ / 0.33 h / 0 °C

2: H₂ / Pd/C / 20 °C

With sulfuric acid; hydrogen; nitric acid; palladium on activated charcoal;

DOI:10.1016/j.bmcl.2007.01.001

upstream raw materials:

6-nitro-4-trifluoromethylquinolin-2(1H)-one

4-(trifluoromethyl)quinolin-2(1H)-one

aniline

4,4,4-trifluoro-3-oxo-N-phenylbutyramide

Downstream raw materials:

6-Dimethylamino-4-trifluoromethyl-2(1H)-quinolinone

Refernces

• 1、 Van Oeveren, Arjan,Motamedi, Mehrnouch,Mani, Neelakandha S.,Marschke, Keith B.,López, Francisco J.,Schrader, William T.,Negro-Vilar, Andrés,Zhi, Lin. "Discovery of 6-N,N-Bis(2,2,2-trifluoroethyl)amino-4- trifluoromethylquinolin-2(1H)-one as a novel selective androgen receptor modulator". . p. 6143 - 6146. Retrieved 2007/10/03.