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

Temperature

15 °C

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.

1. temperatureAfter cooling in an ice bath
2. customthe reaction mixture was quenched with careful addition of water (1 ml) dropwise
3. filtrationThe resulting solid was filtered
4. washwashed several times with tetrahydrofuran
5. concentrationThe filtrate was concentrated
6. customto give oil, which
7. customwas purified by flash chromatography on silica gel using 5% CH3OH(NH3)/ethyl acetate as eluent

ORD record

ord-3064e60a8eef4c049c13ebe9b566a237

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778939B2