2-Chloroethanol → 1-(2-Hydroxyethyl)-4-methylpyridinium chloride

Participants

Reaction Conditions

Reaction Steps

A solution mixture of picoline (0.93 g, 10 mmol) and 2-chloroethanol (4.03 g, 50 mmol) in acetonitrile (20 mL) was heated to 120° C. in a sealed tube overnight. After cooling to room temperature, the solvent was removed under vacuum. The resulting mixture was precipitate from methanol and ethyl acetate to give the desired product 9 (1.5 g) in 87% yield. NMR (400 MHz, DMSO-d6) δ 8.94 (d, J=6.4 Hz, 2H), 7.98 (d, J=6.4 Hz, 2H), 5.55 (br, 1H), 4.64 (t, J=4.8 Hz, 2H), 3.81 (t, J=4.8 Hz, 2H), 2.60 (s, 3H). 13C NMR (400 MHz, DMSO-d6) δ 158.7, 144.2, 127.9, 62.1, 60.0, 21.4.

Provenance & Evidence