Hydrochloric Acid → 2-chloro-4-[N'-(2-ethoxycarbonyl-1-acetylethylidene)hydrazino]benzoic acid

Participants

Reaction Steps

To a suspension of 1 gm. (5.8 mmoles) of 3-amino-4-chlorobenzoic acid in 20 ml. of ethanol was added 5 ml. of water and 1 ml. of 12 N hydrochloric acid. The resultant solution was cooled in an ice bath and to the cooled solution was added in small portions 442 mg. (6.4 mmoles) of sodium nitrite in 3 ml. of water. The mixture was allowed to warm to room temperature and after 30 minutes was added to a suspension of 1.19 gm. (6.4 mmole) of ethyl 3-acetyl-4-oxopentanoate, 1.8 gm. of sodium acetate, 20 ml. of ethanol and 5 ml. of water. The reaction mixture turned dark orange. After stirring for one hour, the mixture was acidified with 3N hydrochloric acid and the resultant solids collected by filtration. After drying the material, 2.53 g. was obtained.

Provenance & Evidence