Aniline → 3-Methyl-N-phenylbut-2-enamide

Participants

Reaction Steps

To a stirred solution of 4.1 g (0.44 mol) of aniline in 200 ml of chloroform, at 25° C., was added slowly a solution of 25 g (0.21 mol) of 3-methylcrotonoyl chloride in 100 ml of chloroform. The reaction mixture was refluxed for 1.5 hours, and then the precipitate was removed by filtration. The chloroform solution was washed successively with 1N hydrochloric acid and saturated sodium bicarbonate solution, and then it was dried (MgSO4) and evaporated in vacuo. This gave 33.5 g (91% yield) of the title compound as a solid, mp 122°-125° C.

Provenance & Evidence