3-Chloroaniline → Acetic acid, chloro[(3-chlorophenyl)hydrazono]-, ethyl ester

Participants

Reaction Conditions

Reaction Steps

12.2 g (149 mmol) sodium acetate trihydrate was added to a solution of 15.5 g (94.1 mmol) ethyl 2-chloroacetoacetate in 300 mL ethanol. The solution was cooled to 0° C. A parallel reaction consisted of the addition of an ice-cold aqueous solution of 6.49 g (94.1 mmol) sodium nitrite in 30 mL water to a solution of 10.0 g (78.4 mol) 3-chloro-phenylamine in 75 mL 6N aqueous HCl. The cold solution of phenyldiazonium chloride was then added to the ester mixture at 0° C. and stirred for 3 h at 0° C. The resulting mixture was diluted with water and ice and stirred for 2 h at 0° C. The precipitate was filtered off, washed with water, dried and used without further purification for the next synthesis step (yield: 13.0 g (64%)).

Provenance & Evidence