4-Fluoroaniline → HCID 178500760, compound

HRID 226961

Reaction equation

HRID 226961 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]([C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([CH3:16])[CH:10]=1)=[CH:5]OC.[F:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1>>[CH3:1][O:2][C:3](=[O:18])[C:4]([C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([CH3:16])[CH:10]=1)=[CH:5][NH:24][C:23]1[CH:25]=[CH:26][C:20]([F:19])=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 97314-FluoroanilineHCID 668792722-(3,4-Dimethyl-benzoyl)-3-methoxy-acrylic acid methyl ester

Product 1

HCID 178500760HCID 178500760, compoundYield 58.9%

Procedure

1 g (4.03 mmol) of the crude 2-(3,4-dimethyl-benzoyl)-3-methoxy-acrylic acid methyl ester 1a and 0.40 g (3.63 mmol) of 4-fluoroaniline were heated neat at 100° C. for 2 h. The reaction solution was cooled to room temperature and the crude product precipitated out of solution. The crude material was recrystallized from dichloromethane/hexane to yield 0.70 g of 2-(3,4-dimethyl-benzoyl)-3-(4-fluoro-phenylamino)-acrylic acid methyl ester 2g as brown crystalline solid.

Workup

  1. customthe crude product precipitated out of solution
  2. customThe crude material was recrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-47d20c46daf14ad09cc6fb0c10cac1b0
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Linked notes

Loading…