C[N:2]([CH:4]=[C:5]1[C:14](=O)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:16](=[O:19])[CH2:17][CH3:18])[CH2:6]1)C.O.[NH2:21]N.C(O)(=O)C>CO>[C:16]([N:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[C:14]2[NH:21][N:2]=[CH:4][C:5]=2[CH2:6]1)(=[O:19])[CH2:17][CH3:18]A mixture of 3-dimethylaminomethylene-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (2.838 g), hydrazine hydrate (0.66 g), and acetic acid (0.792 g) in methanol (30 ml) was stirred at room temperature for 3 hours. To the mixture was added acetic acid (1 ml) and evaporated in vacuo. The residue was dissolved in ethyl acetate, washed successively with aqueous sodium bicarbonate, water, and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was recrystallized from ethyl acetate to give 4,5-dihydro-5-propionyl-1H-pyrazolo[4,3-c]quinoline (1.77 g).
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