S(Cl)(Cl)=O.CN(C=O)C.[CH3:10][C:11]1[N:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:13]=[C:14]2[C:23]=1[C:22]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:16][C:15]2=O.[Cl:31]CCl>C(#N)C>[Cl:31][C:15]1[C:14]2=[N:13][N:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:11]([CH3:10])=[C:23]2[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:16]=1Thionyl chloride (17 mL) and DMF (17 mL) were combined and added dropwise to a mixture of 1-methyl-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one (9.78 g, 35.5 mmol) and dichloromethane (500 mL) at 0° C. The resulting suspension was stirred 5 minutes at 0° C. before warming to ambient temperature and stirring 2 hours. The suspension was concentrated under reduced pressure to afford a tan solid that was stirred in acetonitrile and filtered to obtain 8.8 g of 4-chloro-1-methyl-2-phenyl-2H-pyrazolo[3,4-c]quinoline as a tan solid, mp 208-209° C. MS (APCI) m/z 294 (M+H)+; Anal. calcd for C17H12ClN3.0.05 CH2Cl2: C, 68.72; H, 4.09; N, 14.10. Found: C, 68.85; H, 3.95; N, 14.09.
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