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

Participants

Reaction Steps

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

Provenance & Evidence