C(#N)C.[Cl:4]N1C(=O)CCC1=O.[NH2:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][C:14]=1[O:24][CH3:25]>CCCCCCC.C(OCC)(=O)C>[NH2:12][C:13]1[C:14]([O:24][CH3:25])=[CH:15][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:22][C:23]=1[Cl:4]After adding acetonitrile (170 mL) and N-chlorosuccinimide (13.4 g, 100 mmol) to ethyl 4-amino-3-methoxybenzoate (17.8 g, 91.2 mmol) in that order, the mixture was stirred at 60° C. for 2 hours. The mixture was returned to room temperature, and the solvent in the mixture was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (mixture of n-heptane and ethyl acetate: n-heptane/ethyl acetate=8/1 then 4/1) to obtain the title compound (15.8 g, 68.8 mmol).
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