Hydrochloric Acid → HCID 178500931, compound

Participants

Reaction Steps

A mixture of 2.5 ml of concentrated HCl, 5 ml of H2O, and 5.523 mmoles of aniline (26) was treated with a solution of sodium nitrite 381 mg (5.52 mmoles) in 5 ml of water in an ice bath. This reaction was stirred for two hours to give crude diazonium chloride (27) which was not isolated. The crude diazonium salt solution was poured into a mixture of 961 mg of dimethyl acetonedicarboxylate (2) in 3 ml of ethanol and 3 g of sodium acetate in 10 ml of water with vigorous stirring. Product precipitated immediately. The reaction was allowed to stir for an additional 2 hours, then filtered and dried to give 1.363 g of the desired hydrazone (28) as a solid. MS+: m/e=339.1 (M+H).

Provenance & Evidence