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

Temperature

15 °C

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.

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. customThe residue was purified by flash chromatography on silica gel using 5% CH3OH(NH3)/ethyl acetate as eluent

ORD record

ord-8038adfa05b14ba792bed83e7934ffed

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778939B2