Hydrazine hydrate (1:1) → HCID 178492315, compound

Participants

Reaction Conditions

Reaction Steps

2-hydroxy-4-methoxy-6-methylnicotinonitrile (70 mg, 0.43 mmol) was dissolved in ethanol (10 mL) and was warmed to 55° C. before it was treated with Raney nickel (0.5 mL slurry in water) followed by addition of hydrazine monohydrate (2 mL). The resulting mixture was allowed to stir at 55° C. for 2 hours. The cooled reaction mixture was filtered through diatomaceous earth, rinsed with methanol. The filtrate was concentrated in vacuo to provide crude product which was purified by silica gel column chromatography with dichloromethane/methanol=10:1 to afford 3-(aminomethyl)-4-methoxy-6-methylpyridin-2-ol (40 mg, 56% yield) as a yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 6.04 (s, 1H), 4.87 (br s, 3H), 3.77 (s, 3H), 3.42 (s, 2H), 2.15 (s, 3H).

Provenance & Evidence