Acetic Acid → HCID 178515719, compound

Participants

Reaction Steps

A solution of 30% HBr in AcOH (200 mL) was added dropwise with mechanical stirring at 40° to a solution of N,N-dimethyl-2-(3-cyano-2-pyridyl)ethenamine (10.8 g, 0.062 m) in AcOH (100 mL). After the addition, the slurry was stirred at 55° for 2 hours. The mixture was then evaporated to dryness and the residue treated with ice and saturated aqueous Na2CO3. The aqueous layer was filtered and the filtrate extracted with Et2O. The aqueous layer was placed in a continuous extractor with CHCl3 to yield 7.0 g of a crude product. Sublimation of this product at 160°-180° (0.1 mm) yielded 5.1 g (56%) of hydroxy-1,6-naphthyridine. An analytical sample was prepared by crystallization from CH3OH: m.p. 243-244.5.

Provenance & Evidence