2-Amino-5-chloro-3-nitropyridine → 5-Chloropyridine-2,3-diamine

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A mixture of the nitropyridine 2 (22.0 g 126.8 mmol), Raney Ni (2.2 g) and MeOH (220 mL) was shaken under H2 (20-40 psi) for 3 h, then filtered. The filtrate was rota-evaporated and the residual solid was dried to give 17.57 g (96%) of 3 as a tan powder, mp 169°-171° C. (lit. 172°-173° C, (Israel, M. & Day, A. R., J. Org. Chem. 24:1455-1460 (1959))). 1H NMR (DMSO-d6), 4.991 (bs, 2H), 5.555 (bs, 2H), 6.675 (d, 1H, J=2), 7.196 (d, 1H, J=2).

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