[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Cl.[N:10]([O-])=O.[Na+].C([O-])(=O)C.[Na+].[CH2:19]([O:21][C:22]([C:24]1[C:29](=[O:30])[N:28]2[CH:31]([CH3:35])[CH2:32][CH2:33][CH2:34][C:27]2=[N:26][CH:25]=1)=[O:23])[CH3:20]>O>[CH2:19]([O:21][C:22]([C:24]1[C:29](=[O:30])[N:28]2[CH:31]([CH3:35])[CH2:32][CH2:33][C:34](=[N:10][NH:6][C:5]3[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:27]2=[N:26][CH:25]=1)=[O:23])[CH3:20]To a mixture of 2.5 g. (0.02 mole) of p-chloroaniline and 10 ml. of a 1:1 diluted aqueous hydrochloric acid a solution of 1.4 g. (0.01 mole) of sodium nitrite and 10 ml. of water is slowly added dropwise at 0°-5° C. under stirring. To the reaction mixture 12.0 g. of solid sodium acetate are added in portions, whereupon a solution of 4.7 g. (0.02 mole) of ethyl-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidine-3-carboxylate and 10 ml. of water is slowly added dropwise under vigorous stirring. The reaction mixture is stirred at 0°-5° C. for 2-3 hours, whereupon it is allowed to stand in a refrigerator overnight. The precipitated crystals are filtered off and washed with a small amount of water. After recrystallization from ethanol 4.2 g. (56.0%) of ethyl-9-(p-chloro-phenylhydrazono)-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido-(1,2-a)pyrimidine-3-carboxylate are obtained. Mp.: 177°-178° C.
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