P-Anisidine → HCID 23209186, compound

Participants

Reaction Steps

A mixture of 4-chloro-6-ethoxy-7-methyl-1,8-naphthyridine-3-carbonitrile (2.66 g), 4-methoxyaniline (1.35 g) and IMS (50 ml) was boiled under reflux for 2.5 hours. The mixture was cooled in ice and the precipitate was collected by filtration. This solid was boiled in IMS (50 ml), with 5M sodium hydroxide solution (1.2 ml) under reflux for 30 minutes. The mixture was cooled and evaporated. The residue was purified by flash chromatography on silica using dichloromethane/IMS, 19:1 as the mobile phase to give a solid which was ground up in IMS (15 ml) and filtered to give 6-ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridine-3-carbonitrile, m.p. 190°-192° C. Active (1/1) at 30 mg/kg.

Provenance & Evidence