4-Nitroaniline → HCID 178472851, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-nitroaniline (41.43 g, 0.3 mmol) in water (150 ml) and 37% hydrochloric acid (75 ml) was heated to dissolution. The cooled suspension of hydrochloride salt was treated with sodium nitrite (20.7 g) at -5° C. at a rate which maintained the reaction temperature at -2° C. The diazonium salt solution was added to a solution of ethyl acetoacetate (39 g, 0.3 mmol) in ethanol (225 ml) and ice water (1.5 L) containing sodium acetate (75 g, 0.9 mmol). The mixture thickened and sufficient water was added to permit agitation for 3.5 hours. The mixture was filtered, the filter cake washed with water, and crystallized from ethanol to yield the title compound, (79.16 g), m.p. 128° C.

Provenance & Evidence