Hydrochloric Acid → HCID 88404110, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[2-(2-naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid methyl ester (1.75 g) in pyridine (25 mL) was warmed to dissolve and added semicarbazide hydrochloride (0.7 g). The stirred mixture was heated at 50° C. for 4 hours, cooled, acidified with hydrochloric acid and extracted twice with dichloromethane. The organic layers were washed with dilute hydrochloric acid, combined, dried (Na2SO4), filtered and evaporated to provide a crude mixture of (E) and (Z) isomers. The crude mixture was separated by HPLC (dichloromethane-tetrahydrofuran; 9:1) and the more polar component was crystallized from dichloromethane-methanol to provide 0.6 g of (E)-alpha-[(aminocarbonyl)hydrazono]-4-[2-(2-naphthalenyloxy)ethoxy]benzeneacetic acid methyl ester as a colorless solid, mp 180°-181° C.

Provenance & Evidence