Réaction #1319

Équation de réaction

6-chloronicotinic acid

ethanol

dicyclohexylcarbodiimide

dimethylaminopyridine

→

title compound

Ethyl 6-chloronicotinate

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureat reflux for 2 hours
3. 3
   Températureto cool
4. 4
   Autresolvent removed in vacuo

Mode opératoire

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 dimethylaminopyridine in 200 ml methylene chloride was heated at reflux for 2 hours. The mixture was allowed to cool, solvent removed in vacuo and the residue subjected to flash chromatography to give the title compound as a low-melting white solid. PMR (CDCl3): & 1.44 (3H, t, J~6.2 Hz) 4.44 (2H, q, J~4.4 Hz), 7.44 (1H, d, J~8.1 Hz), 8.27 (1H, dd, J~8.1 Hz, 3 Hz), 9.02 (1H, d, J~3 Hz).

Source