4-(Trifluoromethyl)aniline → HCID 178500756, compound

HRID 226924

Reaction equation

HRID 226924 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]([F:29])([F:28])[C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=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:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]([F:19])([F:28])[F:29])=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 668792722-(3,4-Dimethyl-benzoyl)-3-methoxy-acrylic acid methyl ester

Product 1

HCID 178500756HCID 178500756, compoundYield 16.6%

Procedure

Compound 2c was prepared following the procedure described in Step 2 of Example 1 using 598 mg (2.41 mmol) of the crude 2-(3,4-dimethyl-benzoyl)-3-methoxy-acrylic acid methyl ester 1a and 427 mg (2.65 mmol) of 4-trifluoromethyl-phenylamine. The product 2c was purified by flash chromatography (0-40% ethyl acetate in hexane) to yield 151 mg of 2-(3,4-dimethyl-benzoyl)-3-(4-trifluoromethyl-phenylamino)-acrylic acid methyl ester as a yellow crystalline solid: LC-MSD, m/z for C20H18F3NO3 [M+H]+=378.5; HPLC retention time: 3.0 min.

Workup

  1. customCompound 2c was prepared
  2. customThe product 2c was purified by flash chromatography (0-40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-e14b101489f045c7a4e4237279d4b75e
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Linked notes

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