[Na].[C:2]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)#[N:3].[Cl-:10].[NH4+:11].C(OCC)C>CO>[ClH:10].[C:2]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=[NH:11])[NH2:3]To a solution of sodium (0.23 g) in methanol (40 ml) was added 4-cyanopyridine (10.62 g) at r.t. Stirring was continued for 6 h followed by the addition of ammoniumchloride (5.9 g) and stirring was continued for another 10 h. Then, diethylether (120 ml) was added and the precipitate was filtered off after 30 min and washed with diethylether (20 ml). The product was dried under high vacuum. 4-Amidino-pyridine hydrochloride (14.95 g) was obtained as a white powder.
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