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 ethanol (100 mL), and the reaction heated in a sealed vessel at 170° C. for 20 h. On cooling, the reaction mixture was concentrated under reduced pressure, the residue dissolved in water (200 mL) and acidified to pH 3 with aqueous hydrochloric acid. The aqueous solution was extracted with dichloromethane (4×200 mL), the organic phases combined, dried (Na2SO4) and concentrated under reduced pressure to afford the title compound (27.4 g, 16.4 mmol) as a white solid.

Provenance & Evidence