C(Cl)(=O)C.[C:5]1([NH:11][NH2:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:13][C:14]1[NH:15][C:16]2[C:21]([C:22]=1[C:23](=O)[C:24]([O:26]CC)=O)=[CH:20][CH:19]=[CH:18][CH:17]=2.Cl>C(O)C.CO.C(O)(=O)C>[CH3:13][C:14]1[N:11]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:12]=[C:23]2[C:22]=1[C:21]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:15][C:24]2=[O:26]Acetyl chloride (11.0 mL, 152 mmol), acetic acid (13 mL), and phenylhydrazine (15 mL, 152 mmol) were added sequentially to a suspension of ethyl (2-methyl-1H-indol-3-yl)(oxo)acetate (17 g, 76 mmol) in ethanol (380 mL). The reaction mixture was heated at reflux for 18 hours. After cooling to ambient temperature a red solid was isolated by filtration. The solid was boiled in a 1:1 mixture of 0.5 M hydrochloric acid and methanol and filtered to provide 10.8 g of 1-methyl-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one as a tan solid, mp>250° C. MS (APCI) m/z 276 (M+H)+; Anal. calcd for C17H13N3O: C, 74.17; H, 4.76; N, 15.26. Found: C, 73.95; H, 4.76; N, 15.04.
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