Ethanol → 3-Amino-5-chloropyridine-2-carboxamide

Participants

Reaction Steps

Raney Nickel (10 g of Aldrich 50% slurry in water) was washed with water (100 mL), 5% AcOH (100 mL), water (100 mL), and 95% EtOH (3×100 mL). The resulting slurry was added to a solution of 5-chloro-3-nitropicolinonitrile (104) (5.0 g, 27 mmol) in 95% EtOH (100 mL). The mixture was hydrogenated at 45 psi for 2.5 h. The mixture was then filtered over a bed of Celite and washed with 95% EtOH (2×100 mL). The red/brown filtrate was rota-evaporated to dryness, leaving the title compound as a light brown solid, 3.8 g (82%), mp 152°-6° C. (Lit., 165°-6° C., McCaustland and Cheng, J. Heterocycl. Chem. 7:467 (1970)); 1H NMR (CDCl3): δ5.42 (bs, 1H), 6.05 (bs, 2H), 7.00 (d, J=1.2 Hz, 1H), 7.71 (bs, 1H), 7.79 (d, J=1.2 Hz, 1H).

Provenance & Evidence