[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:14])O[C:11](=[O:13])[CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19]>C(O)(=O)C>[Cl:15][C:16]1[CH:17]=[C:18]([N:19]2[C:11](=[O:13])[CH:12]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=3)[C:9]2=[O:14])[CH:20]=[CH:21][CH:22]=1To a stirred solution of (3-methylphenyl)-furan-2,5-dione (265 mg, 1.41 mmol) in acetic acid (5 ml) at room temperature was added 3-chloroaniline (149 μl, 1.41 mmol). The reaction mixture was heated to reflux and stirred for 3 hours. The reaction mixture was cooled to room temperature. The precipitate formed was filtered, re-suspended in water (15 ml) and recovered by filtration. The precipitate was washed with water (10 ml), heptane (10 ml) and dried under air suction followed by high vacuum.
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