2-Amino-4-chloropyridine → 2-Amino-4-Methoxypyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloropyridin-2-amine (3 g, 23.2 mmol) in DMSO (60 mL) was added sodium methoxide (12.6 g, 232 mmol) and the mixture was then stirred at 150° C. for 3 hours then poured into ice-water. The product was extracted with EtOAc (2×100 mL), and the combined organic layers were washed with water (50 mL) and brine (50 mL), dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography using a solvent system of 50% petroleum ether/EtOAc to give 4-methoxypyridin-2-amine (460 mg, 16%) as a yellow solid MS ESI calcd for C6H8N2O [M+H]+ 125, found 125.

Provenance & Evidence