Water → (6-Aminopyridin-3-yl)methanol

Participants

Reaction Steps

To a solution of 6-aminonicotinic acid ethyl ester (1.18 g, 7.1 mmol) in anhydrous THF (24 mL) was added a solution of lithium aluminum hydride (0.41 g, 10.6 mmol) in THF (12 mL) at 0° C. over 10 min and the mixture stirred for 1.5 h. To the reaction was added sequentially 0.5 mL H2O, 0.5 mL 15% aqueous NaOH and 1.5 mL H2O and the resultant slurry was filtered. The filtrate was dried (MgSO4), filtered, concentrated and purified by column chromatography (10% MeOH/CH2Cl2) to give 6-amino-3-hydroxymethylpyridine (0.61 g, 69%) as colorless crystals. 1H NMR (MeOD) δ 3.31 (s, 1H (OH)), 4.43 (s, 2H), 6.58 (d, 1H, J=8.4 Hz), 7.48 (d, 1H, J=8.7 Hz), 7.85 (s, 1H).

Provenance & Evidence