Methyl chloroformate → Methyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Participants

Reaction Steps

To a solution of 2-chloro-5,6,7,8-tetrahydro-[1,6]naphthyridine hydrochloride (1.54 g, 7.5 mmol) in DCM (25 mL) was added Et3N (3.1 mL, 22 mmol). After the addition and stirring at room temperature for 5 min, the solution was cooled to 0° C., followed by the addition of methylchloroformate (0.85 mL, 11 mmol). The resulting reaction mixture was then allowed to stir at room temperature for 2 hours. It was then washed with satd. aq. NaHCO3 solution and brine. The organic layer was dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product. Flash column chromatography separation (silica gel, 40 g, 30% EtOAc in hexane) then afforded the tile compound (1.53 g, 90%) as a white solid. MS: 227.3 (M+H+).

Provenance & Evidence