[CH3:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Cl.[N:10]([O-])=O.[Na+].[Cl:14][Sn]Cl>O>[ClH:14].[NH:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[N:7][CH:6]=1)[NH2:10]
To a 0° C. solution of 6-methylpyridin-3-amine (12 g, 0.11 mol) in cone HCl (40 mL) was added a solution of NaNO2 (7.7 g, 110 mmol) in water (30 mL) and the resulting mixture was stirred at 0° C. for 1 h. A solution of SnCl2 (50 g, 0.22 mol) in cone HCl (60 mL) was added at 0° C. The reaction solution was warmed to RT and stirred for 2 hours. The precipitate was collected by filtration to provide 5-hydrazinyl-2-methylpyridine hydrochloride (10 g, 57% yield) which was used without further purification.
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