Potassium Hydroxide → 3-Methyl-6-(methylthio)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245152

Reaction equation

HRID 245152 reaction equation
[OH-:1].[K+].[CH3:3][S:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]2=O.[F:16][C:17]([F:29])([F:28])[C:18]1[CH:19]=[C:20]([C:24](=O)[CH2:25][CH3:26])[CH:21]=[CH:22][CH:23]=1>O.C(O)C>[CH3:26][C:25]1[C:24]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:16])([F:28])[F:29])[CH:19]=2)=[N:10][C:11]2[C:7]([C:8]=1[C:9]([OH:14])=[O:1])=[CH:6][C:5]([S:4][CH3:3])=[CH:13][CH:12]=2

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 137064Propiophenone, 3'-(trifluoromethyl)HCID 167812055-(methylthio)-1H-indole-2,3-dione

Product 1

HCID 674183523-Methyl-6-(methylthio)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acidYield 67.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Potassium hydroxide (3.31 g, 59.0 mmol) in water (10 mL) was added slowly to a suspension of 5-(methylthio)-1H-indole-2,3-dione (1.9 g, 9.83 mmol) in ethanol (25 mL). 1-[3-(Trifluoromethyl)phenyl]-1-propanone (1.99 g, 9.83 mmol) was added and the mixture was heated to reflux for 1 h. The solvent was removed under reduced pressure, the residue was dissolved in water, and the aqueous mixture was washed with ether (3 times). The aqueous phase was chilled and was acidified to pH 3 with concentrated HCl. The solid material was collected by filtration, washed with water, and air dried to afford 3-methyl-6-(methylthio)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (2.5 g, 67% yield). MS (m/z) 378.0 (M+H+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 h
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in water
  5. washthe aqueous mixture was washed with ether (3 times)
  6. temperatureThe aqueous phase was chilled
  7. filtrationThe solid material was collected by filtration
  8. washwashed with water, and air
  9. customdried

Sources & evidence

ORD record
ord-20820fad8d1647319b9ca15de2fd2c09
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Linked notes

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