[C:1]([C:4]1[N:9]=[C:8]([CH:10]=[CH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])[CH:7]=[CH:6][CH:5]=1)(=O)[NH2:2].P(Cl)(Cl)(Cl)=O.C(Cl)(Cl)Cl.[OH-].[Na+]>CN(C)C=O>[C:1]([C:4]1[N:9]=[C:8]([CH:10]=[CH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])[CH:7]=[CH:6][CH:5]=1)#[N:2]To a solution of 3-(6-carbamoyl-2-pyridyl)-1-phenyl-2-propen-1-one (0.5 g) in N,N-dimethylformamide (5 ml) was added phosphorus oxychloride (0.46 g) under ice-cooling. After stirring for 30 minutes at same temperature, the solution was poured into a mixture of ice-water (50 ml) and chloroform (10 ml). The resultant solution was adjusted to pH 9 with 4N-sodium hydroxide. The organic layer was washed with water and brine and dried over magnesium sulfate. After evaporating the solvent to give 3-(6-cyano-2-pyridyl)-1-phenyl-2-propen-1-one (0.38 g).
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