[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH3:11])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][N:10]([CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[N+:12]([O-:14])=[O:13])[CH3:11])[CH3:21]A solution of [2-(4-chloro-2-nitro-phenyl)-ethyl]-methyl-amine (29.8 g, 0.14 mole) and ethyl bromoacetate (23.2 g, 0.14 mole) in acetonitrile (500 mL) containing potassium carbonate (9.6 g, 0.07 mole) was stirred at room temperature overnight. The mixture was evaporated in vacuo, water was added to the residue and then extracted with dichloromethane (2×200 mL). The combined organic layers were washed with saturated sodium chloride (300 mL), dried and concentrated. Purification by flash column chromatography (silica gel, methylene chloride) provided 22.5 g of the title compound as a brown oil. 1H NMR (DMSO): 7.98 δ (d, 1H); 7.68 δ (dd, 1H); 7.52 δ (d, 1H); 4.00 δ (m, 2H); 3.20 δ (s, 2H); 2.88 δ (t, 2H); 2.68 δ (t, 2H); 2.25 δ (s, 3H); 1.10 δ (t, 3H).
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