Aniline → 4-Chloro-2-ethylaniline

Participants

Reaction Steps

2'-Ethyl-4'-chloroacetanilide (31 grams) was heated to reflux in a mixture containing 80 milliliters of ethanol and 55 milliliters of concentrated HCL for about 2.5 hours. After cooling to room temperature, the mixture was basified to a pH of about 8 by an aqueous NaOH solution (20 percent). An oily aniline layer was observed. The mixture was transferred to a separatory funnel and was extracted with ether (3 times 75 milliliters). The ethereal extracts were combined and dried over MgSO4. After filtration, ether was removed under reduced pressure. 2-Ethyl-4-chloroaniline was purified and isolated by a reduced pressure distillation, yield 14.2 grams (58 percent).

Provenance & Evidence