3-Chloro-2-methylaniline → N-(o-Chlorobenzylidene)-2-methyl-3-chloroaniline

Participants

Reaction Steps

o-Chlorobenzaldehyde (0.20 mole) is treated with 3-chloro-2-methyl aniline (0.20 mole) with vigorous stirring in a 1 l. Erlenmeyer Flask. After 15 mins., 33 cc of 95% ethanol is added and the reaction mixture is stirred vigorously for an additional 5 mins. The reaction mixture is left standing at room temperature for 10 mins., then it is placed in an ice bath for 0.5 hr. The crystals which formed are collected, washed with 95% ethanol, and air dried. Recrystallization from 85% ethanol gives N-(o-Chlorobenzylidene)-2-methyl-3-chloroaniline. m.p. 83°-85° C.

Provenance & Evidence