[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[C:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1.IC.[CH3:22]COC(C)=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[OH-].[Na+].C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:22])[C:7](=[O:12])[CH:6]=[C:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1A mixture of intermediate 4 (0.045 mol), iodomethane (0.225 mol) and benzyltriethylammonium chloride (0.0045 mol) in NaOH (150 ml) and THF (150 ml) was stirred overnight. EtOAc was added. The mixture was washed with water. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated till dryness. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/EtOAc; 95/5; 20–45 μm). The pure fractions were collected and the solvent was evaporated, yielding 13.5 g (86%) of 6-bromo-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone (intermediate 28), melting point 182° C.
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