N/[C:2](=[CH:5]\[CH3:6])/[C:3]#[N:4].[NH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=1)[NH2:8].C(O)(=O)C>C(O)C>[CH3:6][C:5]1[CH:2]=[C:3]([NH2:4])[N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=2)[N:8]=1To an ice-cold solution of aminocrotononitrile (20.5 g, 0.25 mol) and 2-hydrazino-6-methylpyridine (31.0 g, 0.252 mol) in ethanol (200 mL), acetic acid (30 g, 0.5 mol) was added and the mixture was heated under reflux for 2 hours. The reaction solution was allowed to cool to room temperature, and the reaction solvent was concentrated and evaporated under reduced pressure, and water was added to the residue. The solution was made basic by the addition of an aqueous sodium hydroxide solution, and the organic matter was extracted with ethyl acetate. The extract was washed with saturated brine and water, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (ethyl acetate) to give the title compound (41.3 g, 88% yield).
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