2-Oxobutanoic Acid → HCID 67384166, compound

HRID 245225Notes

Reaction equation

HRID 245225 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[F:10][C:11]([F:21])([F:20])[C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O.O=[C:23]([CH2:27][CH3:28])[C:24]([OH:26])=[O:25]>C(O)C>[CH3:28][C:27]1[C:15]([C:14]2[CH:17]=[CH:18][CH:19]=[C:12]([C:11]([F:21])([F:20])[F:10])[CH:13]=2)=[N:6][C:5]2[C:7]([C:23]=1[C:24]([OH:26])=[O:25])=[CH:8][CH:9]=[C:3]([S:2][CH3:1])[CH:4]=2

Participants

5

Reactant 3

HCID 582-Oxobutanoic AcidHCID 15693Benzenamine, 3-(methylthio)-HCID 679903-(Trifluoromethyl)benzaldehyde

Product 1

HCID 67384166HCID 67384166, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(methylthio)aniline (1.392 g, 10.0 mmol) and 3-(trifluoromethyl)benzaldehyde (1.741 g, 10.0 mmol) in ethanol (30 mL) was stirred at reflux for 1 h. 2-Oxobutanoic acid (1.021 g, 10.0 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 and the solid material collected to give 3-methyl-7-(methylthio)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (0.62 g, 16% yield). MS (m/z) 378.0 (M+H+).

Workup

  1. temperatureat reflux for 1 h
  2. temperatureat reflux for additional 3 h
  3. stirringstirred overnight
  4. filtrationThe mixture was filtered
  5. customthe solid material collected

Sources & evidence

ORD record
ord-3311f21226a64b66b27b61632d986c4d
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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