Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[Cl:7][C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11].C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[CH3:6][O:5][C:3](=[O:4])[CH2:2][NH:11][C:10]1[CH:12]=[CH:13][CH:14]=[C:8]([Cl:7])[CH:9]=1Methyl bromoacetate (8.3 g, 54.3 mmol), 3-chloroaniline (8.31 g, 65.1 mmol) and diisopropylethylamine (7.01 g, 54.3 mmol) were dissolved in N,N-dimethylformamide (20 mL) to give a light yellow solution and the reaction mixture heated at 60° C. overnight. The reaction mixture was cooled to ambient temperature, diluted with ethyl acetate and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give (3-chloro-phenylamino)-acetic acid methyl ester as a solid which was washed with hexanes, filtered and dried (10.2 g, 96%).
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