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

HRID 245200Notes

Reaction equation

HRID 245200 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][C:15]=1[O:21][CH3:22].O=[C:24]([CH2:28][CH3:29])[C:25]([OH:27])=[O:26]>C(O)C>[Br:13][C:14]1[CH:20]=[C:19]2[C:17](=[CH:16][C:15]=1[O:21][CH3:22])[N:18]=[C:6]([C:5]1[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:12])([F:11])[F:1])[CH:4]=1)[C:28]([CH3:29])=[C:24]2[C:25]([OH:27])=[O:26]

Participants

5

Reactant 3

HCID 582-Oxobutanoic AcidHCID 679903-(Trifluoromethyl)benzaldehydeHCID 70182544-Bromo-3-methoxyaniline

Product 1

HCID 673838286-Bromo-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acidYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(Trifluoromethyl)benzaldehyde (21.54 g, 124 mmol) was added to a solution of 4-bromo-3-(methyloxy)aniline (25 g, 124 mmol) in ethanol (300 mL) dropwise. The mixture was stirred at reflux for 1 h, and 2-oxobutanoic acid (12.63 g, 124 mmol) was added portionwise. The reaction mixture was stirred at reflux for additional 3 h, cooled to room temperature, and stirred overnight. The mixture was filtered to collect the precipitate, and the solid was washed with ethanol and dried to give 6-bromo-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (42.6 g, 78% yield). This material was used without further purification. MS (m/z) 442.0 (M+H+).

Workup

  1. temperatureat reflux for 1 h
  2. stirringThe reaction mixture was stirred
  3. temperatureat reflux for additional 3 h
  4. stirringstirred overnight
  5. filtrationThe mixture was filtered
  6. customto collect the precipitate
  7. washthe solid was washed with ethanol
  8. customdried

Sources & evidence

ORD record
ord-1f119455f58945efb2729a1ff4ef5d73
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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