Ethanol → Ethyl 6-chloronicotinate

Participants

Reaction Steps

A mixture of 15.75 g (0.1 mol) 6-chloronicotinic acid, 6.9 g (0.15 mol) ethanol, 22.7 g (0.11 mol) dicyclohexylcarbodiimide and 3.7 g 0.03 mol) dimethylaminopyridine in 200 ml methylene chloride was heated at reflux for 2 hours. The mixture was allowed to cool, solvent removed in vacuo and residue subjected to flash chromatography to give the title compound as a low-melting white solid. PMR (CDCl3): δ1.44 (3 H, t, J~6.2 Hz) 4.44 (2 H, q, J~6.2 Hz), 7.44 (1 H, d, J~8.1 Hz), 8.27 (1 H, dd, J~8.1 Hz, 3 Hz), 9 02 (1 H, d, J3 Hz).

Provenance & Evidence