Methanol → 2-Methyl-7-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid

HRID 841773Notes

Reaction equation

HRID 841773 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:35])=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[C:11]([NH:16][C:17]([C:19]1[C:20]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:18])[CH:10]=2)=[O:5])C.CO.O.O.[OH-].[Li+]>O1CCCC1>[CH3:35][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:15][C:14]2[C:9](=[CH:10][C:11]([NH:16][C:17]([C:19]3[C:20]([C:25]4[CH:26]=[CH:27][C:28]([C:31]([F:33])([F:32])[F:34])=[CH:29][CH:30]=4)=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:18])=[CH:12][CH:13]=2)[N:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 698903792-Methyl-7-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 227368472-Methyl-7-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acidYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methyl-7-[(4′-trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid ethyl ester (345 mg, 0.72 mmol) was dissolved in 3 ml of tetrahydrofuran, 1 ml of methanol and 1 ml of water, and lithium hydroxide monohydrate was added (61 mg, 1.44 mmol). After 3 h at room temperature, the volatiles were evaporated and the resulting mixture diluted with 10 ml of water before being brought to pH 1 with 1N HCl. Filtration of the resulting solid followed by air drying afforded 326 mg of the title compound as a yellow solid.

Workup

  1. customthe volatiles were evaporated
  2. additionthe resulting mixture diluted with 10 ml of water
  3. filtrationFiltration of the resulting solid
  4. customdrying

Sources & evidence

ORD record
ord-a6db6c14e49e43488a2fb500e2516fc9
Source dataset
uspto-grants-2002_04
Patent number
US06369075B1

Reaction notes

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