HCID 178500760, compound → 3-(3,4-dimethylbenzoyl)-6-fluoroquinolin-4(1H)-one

HRID 226962

Reaction equation

HRID 226962 reaction equation
CO[C:3](=[O:24])[C:4]([C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=1)=[CH:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1>C1(OC2C=CC=CC=2)C=CC=CC=1.CCCCCC>[CH3:22][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[CH3:21])[C:14]([C:4]1[C:3](=[O:24])[C:8]2[C:7](=[CH:12][CH:11]=[C:10]([F:13])[CH:9]=2)[NH:6][CH:5]=1)=[O:23]

Participants

4

Reactant 1

HCID 178500760HCID 178500760, compound

Product 1

HCID 46065703-(3,4-dimethylbenzoyl)-6-fluoroquinolin-4(1H)-oneYield 66.1%

Reagents, catalysts & solvents 2

HCID 7583Diphenyl EtherSolventHCID 8058HexaneSolvent

Procedure

0.691 g (2.11 mmol) of 2-(3,4-Dimethyl-benzoyl)-3-(4-fluoro-phenylamino)-acrylic acid methyl ester 2g was dissolved in 30 mL of diphenyl ether and the resultant solution was heated at 250° C. After 2.5 h the solution was cooled to room temperature and diluted with 50 mL of hexane. The crude product precipitated out of solution and was isolated by filtration. The crude product was further washed with hexane to yield 0.412 g of 3-(3,4-dimethyl-benzoyl)-6-fluoro-1H-quinolin-4-one 3j as a brown solid.

Workup

  1. customThe crude product precipitated out of solution
  2. customwas isolated by filtration
  3. washThe crude product was further washed with hexane

Sources & evidence

ORD record
ord-07f7734ea7a1418e94850b8843af144c
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Linked notes

Loading…