Malonic Acid → 7-Nitro-1,2,3,4-tetrahydroisoquinoline-1-acetic acid

Participants

Reaction Conditions

Reaction Steps

A suspension of 7-nitro-3,4-dihydroisoquinoline (10.0 g, 56.1 mmol) and malonic acid (11.7 g, 112 mmol) in acetic acid (55 ml) was heated at 120° C. for 0.5 h. Upon cooling, the solvent was concentrated to give a red oil which was taken up in aqueous ethanol (50 ml of 75%). After crystallization had occurred, the solvent was cooled to 0° C. and the product collected. The title compound was isolated as a tan solid (10.9 g, 81%), m.p. 264-5° C. (dec.).

Provenance & Evidence