Dimethyl acetylenedicarboxylate → HCID 178498488, compound

Participants

Reaction Steps

A solution of acetylene dicarboxylic acid dimethyl ester (2.8g.) in dry methanol (20ml.) was added to a solution of 2,6-diamino-1-methylbenzene (1.2g.) in dry methanol (20ml.), and the mixture heated under reflux for 3 hours. The mixture was then cooled and filtered, and the solid residue of bis anil (1.9g., m.p. 194°-196°C., crystallised from dimethylformamide) was added in portions to boiling diphenyl ether (50ml.), and the mixture was kept at 240°-145°C. for 10 minutes. The mixture was then cooled, and filtered, and the solid residue was washed with petroleum ether (b.p. 40°-60°C.; 750ml.), and crystallised from dimethylsulphoxide to give 2,8-dimethoxycarbonyl-4,6-dihydroxy-10-methylpyrido[3,2-g]quinoline, m.p. 296°C.

Provenance & Evidence