Ethyl 4-amino-6-chloronicotinate → (4-Amino-6-chloropyridin-3-yl)methanol

Participants

Reaction Steps

Treat a 0° C. suspension of lithium aluminum hydride (5.7 g, 150 mmol) in THF (150 mL), under N2, drop-wise with a solution of ethyl 4-amino-6-chloronicotinate (15 g, 75 mmol) in THF (50 mL), allow to warm to RT and stir for 3 h. Quench the mixture with 10% NaOH (5.7 mL), then water (5.7 mL), filter to remove solids, add water to the filtrate and extract with EtOAc (3×). Wash the combined organics with brine, dry and concentrate to give the title compound (10 g, 84%). 1H NMR (300 MHz, DMSO-d6): δ 7.79 (s, 1H), 6.53 (s, 1H), 6.17 (s, 2H), 5.10 (t, J=5.4 Hz, 1H), 4.36 (d, J=5.4 Hz, 2H).

Provenance & Evidence