(2-Amino-pyridin-4-yl)-methanol

6937-03-7

105250-17-7

General procedure for the synthesis of 2-amino-4-pyridinemethanol from methyl 2-aminoisonicotinate: 26 g of lithium aluminum hydride was dissolved in 800 mL of anhydrous tetrahydrofuran (THF). Under stirring conditions, 103 g of 2-aminoisonicotinic acid methyl ester dissolved in 600 mL of anhydrous THF was slowly added, and the resulting slurry was heated to reflux for 3 hours. Upon completion of the reaction, the reaction was quenched by careful addition of cooling water, and the precipitate was collected by filtration and washed with 300 mL of THF. The filtrates were combined and concentrated under reduced pressure and the residue was recrystallized from benzene. The product was obtained as 61 g in 73% yield with a melting point of 80-81.5°C. The product was analyzed by 1H NMR (DMSO-d6, δ, ppm): 4.36 (s, 2H), 5.19 (s, 1H), 5.78 (s, 2H), 6.40 (d, 1H), 6.46 (s, 1H), 7.81 (d, 1H).13C NMR (DMSO- d6, δ, ppm): 62.3, 105.2, 110.3, 147.7, 152.7, 160.3. Elemental analysis results (%): C 57.63, H 6.32, N 22.68; theoretical values (C6H8N2O): C 58.05, H 6.40, N 22.56.