Methanol → Methyl 2-chloronicotinate

Participants

Reaction Steps

To a suspension of 2-chloronicotinic acid 3 (15.8 g, 0.1 mol) in 100 ml of dry MeOH at 0° C. was added thionyl chloride (17.8 g, 0.15 mol) dropwise. The reaction was then slowly warmed to room temperature and stirred for 2 days. The solvent was then removed via vacuum and the residue was dissolved in sat. NaHCO3. The resulted basic solution was then extracted with EtOAc (3×100 ml). The combined organic phases were washed with brine, dried with NaSO4, concentrated via vacuum to give 2-chloronicotinic methyl ester 4(15.3 g, 89%) as an oil: 1H NMR (CDCl3, 300 MHZ) δ 8.52 (dd, J=1.8, 4.5 Hz, 1H), δ 8.19 (dd, J=2.1, 7.8 Hz, 1H), δ 7.38 (dd, J=4.8, 7.8 Hz, 1H), δ 3.97 (s, 3H)

Provenance & Evidence