4-(Trifluoromethyl)aniline → N-[4-(trifluoromethyl)phenyl]-3-oxopentanoic acid amide

Participants

Reaction Conditions

Reaction Steps

Methyl 3-oxopentanoate 10.0 g (76.8 mmol) was heated to 115° C. and 4-(trifluoromethyl)aniline 12.83 g (79.6 mmol) was added dropwise thereto for 10 minutes. After stirring at the same temperature for 25 minutes, toluene (50 mL) was added and the resulting reaction solution was further heated and stirred for 12 hours. The reaction solution was cooled to 0° C. to precipitate a solid and subjected to vacuum filtration to obtain N-[4-(trifluoromethyl)phenyl]-3-oxopentanoic acid amide as a white solid (11.22 g, isolated yield: 57%). 1H-NMR (CDCl3, 400 MHz/ppm): δ 1.13 (3H, t), 2.64 (2H, q), 3.60 (2H, s), 7.58 (2H, d), 7.69 (2H, d), 9.52 (1H, br)

Provenance & Evidence