Hydrochloric Acid → Ethyl 6-ethoxy-4-(4-methoxyanilino)-1,5-naphthyridine-3-carboxylate hydrochloride

Participants

Reaction Steps

A mixture of ethyl 4-chloro-6-ethoxy-1,5-naphthyridine-3-carboxylate (17.95 g), 4-methoxyaniline (8.29 g), anhydrous potassium carbonate (18.6 g) and THF (250 ml) was stirred at ambient temperature for 48 hours. The mixture was evaporated to dryness and water was added to the residue. The mixture was extracted with dichloromethane to give a solid which was dissolved in IMS (50 ml). The solution was saturated with hydrogen chloride gas whilst cooling the mixture in ice. Ether was added to induce precipitation. The solid was collected by filtration to give ethyl 6-ethoxy-4-(4-methoxyanilino)-1,5-naphthyridine-3-carboxylate hydrochloride, m.p. 160°-162° C. Active (3/3) at 30 mg/kg.

Provenance & Evidence