Benzoyl chloride → N-(6-Methyl-5,6,7,8-tetrahydro[1,6]naphthyridin-3-yl)-benzamide

Participants

Reaction Steps

3-Amino-6-methyl-5,6,7,8-tetrahydro[1,6]naphthyridine (314 mg, 1.9 mmol) was dissolved in dichloromethane (10 ml) and treated sequentially with triethylamine (214 mg; 2.1 mmol) and benzoyl chloride (297 mg; 2.1 mmol). The mixture was stirred at ambient temperature until tlc showed no starting material remaining. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate, water, saturated brine, dried (anhydrous magnesium sulphate) and evaporated to dryness under reduced pressure. Chromatography through silica gel, eluting with methanol in dichloromethane (0 to 50% methanol gradient), gave the title compound as an off-white foam (269 mg; 52%)

Provenance & Evidence