Glycerol → 2-Methyl-1,5-naphthyridine

Participants

Reaction Steps

A mixture of 6-methylpyridin-3-amine (8-1) (4.8 g, 44.4 mmol) and propane-1,2,3-triol (20 g, 222 mmol) in 5 mL of H2O was stirred at room temperature for 5 min, then concentrated H2SO4 (47 g, 488 mmol) was added dropwise within 20 min at room temperature. After addition, the reaction mixture was stirred at 150° C. for 30 min. After cooled to room temperature, the mixture was poured into water, adjusted with 6 N NaOH to pH 13, then extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, concentrated and purified by chromatography on silica gel to afford the title compound (2.9 g). MS: 145 (M+1)+.

Provenance & Evidence