C(Cl)CCl.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13]1[C:22]([C:23](O)=[O:24])=[CH:21][C:20]2[C:15](=[CH:16][C:17]([O:26]C)=[CH:18][CH:19]=2)[N:14]=1.[CH:28]1[CH:29]=[CH:30][C:31]2N(O)N=[N:34][C:32]=2[CH:33]=1.NC1C=CC=CC=1>CN(C=O)C.C(Cl)Cl>[C:32]1([NH:34][C:23]([C:22]2[C:13]([NH:12][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[Cl:5])=[N:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[C:17]([OH:26])[CH:16]=3)=[O:24])[CH:33]=[CH:28][CH:29]=[CH:30][CH:31]=1EDC (633 mg, 3.3 mmol) was added to a solution of 2-(2-Chloro-phenylamino)-7-methoxy-quinoline-3-carboxylic acid (986 mg, 3.0 mmol), HOBt (446 mg, 3.3 mmol) and aniline (307 mg, 3.3 mmol) in DMF (5 ml) at room temperature. After stirring the mixture for 1 hr, CH2Cl2 was used to extract the reaction mixture, and washed with water, saturated brine and then dried with magnesium sulfate. The solvent was removed under reduced pressure to give yellow oil. The yellow oil was purified by chromatography on SCX column using MeOH as eluent. At last, 2-(2-Chloro-phenylamino)-7-hydroxy-quinoline-3-carboxylic acid phenylamide was obtained as yellow solid after recrystallization from CH2Cl2 and Hexane; 947 mg (78%).
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