Methanol → Methyl 6-methylnicotinate

Participants

Reaction Steps

A solution of 6-methyl nicotinic acid, 2-1 (5 g, 36.5 mmol) in 100 ml of anhydrous methanol was placed in a 250 ml three neck flask equipped with a dropping funnel vertical condenser and CaCl2 drying tube. The reaction solution was cooled to -15° in an ice acetone bath and SOCl2 (5 ml, 69.1 mmol) was added dropwise. The solution was then heated at reflux for 3 h then cooled and the solvent removed at reduced pressure. The resulting white solid was treated with 60 ml of saturated NaHCO3 and extracted into CH2Cl2 (3×50 ml). The pooled extracts were dryed (Na2SO4 ), filtered and evaporated at reduced pressure. The resulting oil crystallized on standing giving 2-2 as a white solid.

Provenance & Evidence