2-Chloronicotinic acid → 2-Ethoxynicotinic Acid

Participants

Reaction Conditions

Reaction Steps

A solution of potassium t-butoxide (44.9 g, 0.40 mol) in absolute ethanol (300 ml) was added slowly to a solution of 2-chloronicotinic acid (30 g, 0.19 mol) in absolute ethanol (100 ml) and the reaction mixture heated in a sealed vessel at 170° C. for 20 hours, then allowed to cool. The resulting mixture was evaporated under reduced pressure, the residue dissolved in water (200 ml) and the solution acidified to pH 3 with hydrochloric acid and extracted with dichloromethane (4×200 ml). The combined extracts were dried (Na2SO4) and evaporated under reduced pressure to give the title compound (27.4 g, 41%) as a white solid. δ (CDCl3): 1.53 (3H,t), 4.69 (2H,q), 7.13 (1H,m), 8.37 (1H,d), 8.48 (1H,d).

Provenance & Evidence