Aniline → HCID 178418256, compound

Participants

Reaction Conditions

Reaction Steps

A solution of aniline (37.2 g, 0.4 mmol) in water (32 ml) and concentrated hydrochloric acid (100 ml) was poured into ice (400 g). The 0° C. solution was treated with a solution of sodium nitrite (27.6 g, 0.4 mmol) in water (50 ml). The diazonium salt solution was poured rapidly into a stirred solution of ethyl acetoacetate (52 g, 0.4 mmol) in ethanol (300 ml) and ice water (1.0 L) containing sodium acetate (100 g, 1.2 mmol). Th mixture was stirred at 0° C. for 2.5 hours, filtered, and the filter cake was crystallized from ethanol to yield the title compound (75.2 g), m.p. 75°-76° C. (lit 61°-64° C.).

Provenance & Evidence