4-Cyanopyridine → Pyridine-4-amidine hydrochloride

Reaction equation

C[O-].[Na+].[C:4]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)#[N:5].[Cl-:12].[NH4+:13]>CO>[ClH:12].[C:4]([NH2:13])(=[NH:5])[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1

Participants

Procedure

Sodium methoxide (0.54 g) and 4-cyanopyridine (10.4 g) were combined in anhydrous methanol (100 ml) and stirred at room temperature for 18 h, under a nitrogen atmosphere. Ammonium chloride (5.99 g) was then added, and the mixture heated to reflux for 4 h, under a calcium chloride guard tube. The reaction was cooled, evaporated under reduced pressure, re-suspended in ethanol (120 ml) and heated to reflux for another 15 min. The resultant white precipitate was filtered off, dried, then triturated with ice-cold water and dried under vacuum at 40° C. to yield the title compound as a white solid (7.44 g, 47%). Two further crops were obtained through concentration of the ethanol filtrate (total yield 12.1 g, 77%)