3-Aminoisonicotinic acid → (3-Aminopyridin-4-yl)methanol

Participants

Reaction Conditions

Reaction Steps

3-Aminoisonicotinic acid (1 g, 7.24 mmol) was carefully added in 3 aliquots to a slurry of LiAlH4 (0.99 g, 26.1 mmol) in dry tetrahydrofuran (40 ml). The resulting mixture was stirred at 15° C. overnight. After cooling in an ice bath, the reaction mixture was quenched with careful addition of water (1 ml) dropwise, followed by 15% aqueous NaOH (1 ml), and then water (3 ml). The resulting solid was filtered, and washed several times with tetrahydrofuran. The filtrate was concentrated to give oil, which was purified by flash chromatography on silica gel using 5% CH3OH(NH3)/ethyl acetate as eluent to yield the title compound as a yellow oil. 610 mg.

Provenance & Evidence