Potassium Hydroxide → 6-Bromo-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245149Notes

Reaction equation

HRID 245149 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[NH:7][C:6](=[O:13])[C:5]2=O.[OH-:15].[K+].[F:17][C:18]([F:30])([F:29])[C:19]1[CH:20]=[C:21]([C:25](=O)[CH2:26][CH3:27])[CH:22]=[CH:23][CH:24]=1>CCO.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[N:7]=[C:25]([C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([C:18]([F:17])([F:29])[F:30])[CH:20]=1)[C:26]([CH3:27])=[C:5]2[C:6]([OH:13])=[O:15]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 137064Propiophenone, 3'-(trifluoromethyl)HCID 145950615-bromo-6-methoxy-1H-indole-2,3-dione

Product 1

HCID 673838286-Bromo-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acidYield 44.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 5-bromo-6-(methyloxy)-1H-indole-2,3-dione (75 g, 293 mmol), KOH (98.5 g, 1760 mmol) in EtOH (500 mL) and H2O (150 mL) was stirred followed by the addition of 1-[3-(trifluoromethyl)phenyl]-1-propanone (59 g, 293 mmol) in one portion. After refluxing for 16 h, the mixture was evaporated to remove EtOH and pH adjusted to 3 with 2N HCl. Following filtration to yield the crude product, the material was refluxed in EtOH (1 L) for 1 h, filtered and dried to yield 6-bromo-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (57 g, 44% yield) as an off white solid. MS (m/z) 440 (M+H+).

Workup

  1. temperatureAfter refluxing for 16 h
  2. customthe mixture was evaporated
  3. customto remove EtOH
  4. filtrationfiltration
  5. customto yield the crude product
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-0efd84bacb604f3486499c2a8def17b4
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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