Propionic Acid → 4-Propylamino-3-pyridinol N,N-diethylcarbamate

Participants

Reaction Conditions

Reaction Steps

A solution of propionic acid (58.5 ml) in 100 ml of benzene was treated with NaBH4 (9.6 g added portionwise). After the frothing subsided, 4-amino-3-pyridinol N,N-diethylcarbamate (5.30 g) was added and the mixture was heated at 80° C. for 2 hours. The reaction mixture was poured into a dilute NaOH solution and the aqueous phase was extracted with ethyl acetate (3×). The combined organics were washed with water and dried (saturated NaCl, MgSO4). The desired amine was purified via flash chromatography to give 3.2 g of solid, m.p. 60°-70° C. This product was combined with a crop obtained from another run and recrystallized from hexane to give analytically pure material, m.p. 75°-78° C.

Provenance & Evidence