[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:21]([O:20][C:18](=[O:19])[C:17]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:23])[CH3:22]To a solution of 4-chloroaniline (1.16 g) in methylene chloride (26 mL) were sequentially added triethylamine (1.52 mL) and ethyl chlorooxoacetate (1.11 mL) under ice cooling, and the thus-obtained mixture was stirred at room temperature for 14 hours. Saturated aqueous sodium hydrogencarbonate was added to the reaction mixture to partition the mixture. The organic layer was sequentially washed with 10% aqueous citric acid and saturated brine, and was dried over sodium sulfate anhydrate. The solvent was concentrated under reduced pressure, and hexane was added to the residue. The precipitated crystals were collected by filtration, and were dried, to thereby give the title compound (1.89 g).
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