2-Chlorophenylhydrazine hydrochloride → HCID 86594817, compound

Participants

Reaction Conditions

Reaction Steps

4-(4-Chlorophenyl)-2-hydroxy-4-oxobut-2-enoic acid ethyl ester lithium salt (10 g, 38.37 mmol) was dissolved in acetic acid (400 ml). After the solution was cooled to 10° C. with an ice-water bath, a concentrated aqueous solution of sodium nitrite (2.86 g, 40.29 mmol) was added dropwise, keeping the temperature between 10 and 15° C. The reaction mixture was stirred for another 45 minutes, and 2-chlorophenylhydrazine HCl salt (8.5 g, 46.04 mmol) was added in portions. Stirring was continued for 3 hours. Upon completion of the reaction, the reaction mixture was poured into 600 ml ice-cold water. A yellow solid precipitated and after 2 hours, it was collected, washed with water, and dried to give crude 4-(4-chlorophenyl)-2-[(2-chlorophenyl)hydrazono]-3-nitroso-4-oxobutyric acid ethyl ester which was used in the next step without further purification.

Provenance & Evidence