Isobutyric Acid → 4-((2-Methylpropyl)amino)-3-pyridinol N,N-diethylcarbamate

Participants

Reaction Conditions

Reaction Steps

A solution of isobutyric acid (49.85 g) in 100 ml of benzene was treated with NaBH4 (6.91 g added portionwise). After the frothing subsided, 4-amino-3-pyridinol N,N-diethylcarbamate (4.90 g) was added and the mixture was heated at 85° C. for 3 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 2.05 g of solid. This product was recrystallized from hexane to give analytically pure material, m.p. 71°-75° C.

Provenance & Evidence