N-Ethyl-/>-chloroformanilide

B. N-Ethyl-p-chloroaniline. In a 500-ml. round-bottomed flask are placed 70 g. (0.38 mole) of N-ethyl-/>-chloroformanilide and 170 ml. of 10% hydrochloric acid. The mixture is heated under reflux for 1 hour, cooled, then neutralized, and finally made basic with 15% potassium hydroxide solution. The lower layer of N-ethyl- -chloroaniline is separated, and the aqueous layer is saturated with potassium carbonate and extracted with two 200-ml. portions of ether. The ether extracts are combined with the bulk of the product, washed with two 100-ml. portions of water, and then dried over calciiun chloride. After the ether has been removed by distillation, the residue is distilled at reduced pressure from a 125-ml. Claisen flask. N-Ethyl- -chloroaniline is collected at 108-110°/5 mm. or 149-150°/40 mm., 1.5650-1.5661, weight 52-55 g. (87-92%) (Note 5). 

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