Hydroxyamine hydrochloride → 3-Amino-2-(amino(hydroxyimino)methyl)pyridine

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A suspension of 3-amino-2-cyanopyridine (1.18 g, 9.9 mmol), sodium methoxide (0.64 g, 12 mmol) and hydroxylamine hydrochloride (0.83 g, 12 mmol) in ethanol (10 ml) was heated under reflux for 1 h. The mixture was filtered and the filtrate concentrated to an oil, which was purified by flash column chromatography on silica gel, eluting with dichloromethane/methanol (50:1 to 10:1) as eluent to afford the product as a yellow solid (0.82 g), MS (+CI) m/z 153 [M+H]+; 1H NMR (d6-DMSO) 9.80 (1H, br. s), 7.80 (1H, dd), 7.10 (1H, d), 7.08 (1H, d), 6.62 (2H, s), 5.90 (1H, s).

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