C[O-].[Na+].[C:4]([C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]2[CH:17]=[C:16]([C:18]#[N:19])[CH:15]=[CH:14][N:13]=2)[CH:7]=1)#[N:5].[Cl-:20].[NH4+:21].[NH3:22]>CO.C(O)(=O)C>[ClH:20].[ClH:20].[C:18]([C:16]1[CH:15]=[CH:14][N:13]=[C:12]([C:8]2[CH:7]=[C:6]([C:4](=[NH:22])[NH2:5])[CH:11]=[CH:10][N:9]=2)[CH:17]=1)(=[NH:21])[NH2:19]
0.5 ml of 1.1N sodium methoxide in absolute methanol is added to a suspension of 1.2 g (0.0058 mol) of 4,4'-dicyano-2,2'-bipyridine in 48 ml of absolute methanol and the whole is boiled for 5 hours under reflux. 0.05 ml of glacial acetic acid, 0.72 g (0.0134 mol) of ammonium chloride and 10 ml of 4.6N methanolic ammonia solution are then added to the solution while it is still warm and the whole is boiled for a further one hour. The cooled reaction mixture is concentrated by evaporation, taken up in 60 ml of 0.1N hydrochloric acid, filtered and applied to a column of 250 ml of Amberlite® ER 180 adsorber resin. Washing is effected with distilled water and 5 ml fractions are collected. Fractions 14-21 are combined and concentrated by evaporation and the residue is crystallised from a small amount of water to give the title compound; m.p. >280°.
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