[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.Cl.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][NH2:18])=[CH:13][CH:12]=1.C([O-])(=O)C.[Na+]>C(O)C>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][N:18]=[CH:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:13][CH:12]=12.2 g of 3-pyridinecarbaldehyde was dissolved in 100 ml of ethanol. The solution was added to a filtered solution of 3.6 g of p-chlorophenylhydrazine hydrochloride and 9.8 g of sodium acetate in 60 ml of 50% by volume aqueous ethanol. The resulting precipitated solid was collected and recrystallized from ethanol to give 1, as a pale yellow prisms, mp 186° C.
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