[Cl-].[Al+3].[Cl-].[Cl-].C([N:12]1[C:17](=[O:18])[CH:16]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH:14]=[N:13]1)C1C=CC=CC=1>C1(C)C=CC=CC=1>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:15]2[CH:14]=[N:13][NH:12][C:17](=[O:18])[CH:16]=2)=[CH:20][CH:21]=1Aluminum chloride (11.4 g, 86 mmol) was added to a stirred mixture of 2-benzyl-5-(4-fluorophenyl)pyridazin-3(2H)-one (4.0 g, 14.3 mmol) in toluene (285 ml) and the mixture was stirred at 70° C. for 1 h. After cooling, the reaction was cooled in an ice bath and quenched slowly with water (50 mL). The precipitate was filtered, washed with water, and dried under high-vacuum to afford the title compound. 1H NMR (500 MHz, CD3SOCD3) δ 8.28 (d, 1H); 7.88 (dd, 2H); 7.35 (t, 2H); 7.13 (d, 1H). LRMS (APCI) calc'd for (C10H8FN2O) [M+H]+, 191.1. found 191.1.
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