Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.O.[NH2:11][NH2:12]>>[NH:11]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1)[NH2:12]A mixture of 6-chloro-nicotinonitrile (2.77 g, 20 mmol) and hydrazine hydrate (15 mL) was stirred at 100° C. for 3 h and evaporated. The residue was suspended in ether and filtered, then suspended in sodium bicarbonate solution and filtered, washing with water, and dried to provide 6-hydrazino-nicotinonitrile (1.25 g, 46% yield) as a tan solid. 1H-NMR (DMSO-d6, 500 MHz) 8.59 (s, 1H), 8.35 (s, 1H), 7.74 (d, 1H), 6.75(s, 1H), 4.44 (s, 2H) ppm; MS (FIA) 135.1 (M+H).
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