Cl[C:2]([C:4]1[C:5]([Cl:15])=[C:6]([CH:11]=[CH:12][C:13]=1[Cl:14])[C:7]([O:9][CH3:10])=[O:8])=[O:3].Cl.[CH2:17]([O:20][NH2:21])[CH2:18][CH3:19].C(N(CC)CC)C>C(Cl)Cl>[Cl:15][C:5]1[C:4]([C:2]([NH:21][O:20][CH2:17][CH2:18][CH3:19])=[O:3])=[C:13]([Cl:14])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]10.7 g (0.04 mol) of methyl 3-chlorocarbonyl-2,4-dichlorobenzoate in 100 ml of methylene chloride were slowly added dropwise at 30° C. to a solution of 4.50 g (0.04 mol) of propoxyamine hydrochloride and 4.05 g (0.04 mol) of triethylamine in 200 ml of methylene chloride. After the reaction mixture had been stirred for 2 hours at room temperature, it was washed with dilute phosphoric acid, dried and concentrated. The resulting residue was chromatographed on silica gel (eluent: toluene/ethyl acetate=9/1). This gave 11.50 g of methyl 2,4-dichloro-3-(N-propoxyamino)carbonylbenzoate.
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