Hexane → 3-(3,4-dimethyl-benzoyl)-6-trifluoromethyl-1H-quinolin-4-one

HRID 226925

Reaction equation

HRID 226925 reaction equation
CO[C:3](=[O:27])[C:4]([C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]([CH3:25])[CH:19]=1)=[CH:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.CCCCCC>[N+](C1C=CC=CC=1)([O-])=O>[CH3:25][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[CH3:24])[C:17]([C:4]1[C:3](=[O:27])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([F:16])([F:14])[F:15])[CH:11]=2)[NH:6][CH:5]=1)=[O:26]

Participants

4

Reactant 2

HCID 8058HexaneHCID 178500756HCID 178500756, compound

Product 1

HCID 577545723-(3,4-dimethyl-benzoyl)-6-trifluoromethyl-1H-quinolin-4-oneYield 83.3%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

2-(3,4-dimethyl-benzoyl)-3-(4-trifluoromethyl-phenylamino)-acrylic acid methyl ester 2c (151 mg, 0.40 mmol) was refluxed in 5 mL of nitrobenzene for 3 h, then cooled down and to it was added 10 mL of hexane. The crude product precipitated out of solution and was isolated by filtration. The crude product was washed with hexane to give 115 mg of 3-(3,4-dimethyl-benzoyl)-6-trifluoromethyl-1H-quinolin-4-one as off-white crystals 3b: LC-MSD, m/z for C19H14F3NO2, [M+H]+=346.4,; HPLC retention time: 2.3 min.

Workup

  1. temperaturecooled down and to it
  2. customThe crude product precipitated out of solution
  3. customwas isolated by filtration
  4. washThe crude product was washed with hexane

Sources & evidence

ORD record
ord-8210f470565e403ca28d530672deff0a
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Linked notes

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