4-Aminobenzoic Acid → HCID 178472850, compound

Participants

Reaction Steps

4-Amino-benzoic acid (40 g, 0.28 mol) was dissolved in a mixture of concentrated hydrochloric acid (84 ml) and water (84 ml). To the resulting mixture was added dropwise at 5° C. a solution of sodium nitrite (21.5 g, 0.31 mol) in water (100 ml). The resulting diazonium salt was added to a mixture of sodium acetate (116 g, 0.85 mol), ethanol (300 ml) and ethyl acetoacetate (36.5 ml, 0.28 mol) at room temperature. The resulting mixture was diluted with a 50% aqueous ethanol (1 l) and stirred for 1 h at room temperature. The precipitate was filtered off and washed with water (1 l), 50% aqueous ethanol (1 l) and heptane (2×300 ml) and dried in vacuo at 50 ° C. for 48 h affording 77 g (98%) of 4-[N′-(1-ethoxycarbonyl-2-oxo-propylidene)-hydrazino]-benzoic acid as a solid.

Provenance & Evidence