Aniline → methyl 3-anilino-2-(3,4-dimethylbenzoyl)prop-2-enoate

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Reaction Steps

Crude 2-(3,4-dimethyl-benzoyl)-3-methoxy-acrylic acid methyl ester 1a(13.7 g, 55.1 mmol) and of aniline (5.12 g, 55.1 mmol) were heated neat at 100° C. for 30 minutes, then cooled down to room temperature and recrystallized from dichloromethane/hexane to yield 7.94 g of 2-(3,4-Dimethyl-benzoyl)-3-phenylamino-acrylic acid methyl ester 2a as a yellow crystalline solid: LC-MSD, m/z for C19H19NO3 [M+H]+=310.4; HPLC retention time: 2.8 min.

Provenance & Evidence