3-Aminopicolinic acid → (3-Aminopyridin-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

3-Aminopicolinic acid (145 mg, 1.05 mmol) was carefully added in 3 aliquots to a slurry of LiAlH4 (143 mg, 3.78 mmol) in dry tetrahydrofuran (6 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. The residue 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. 110 mg.

Provenance & Evidence