Cl.[Cl-].[NH4+].[Br:4][C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[C:8]([CH3:14])=[CH:7][C:6]=1[N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>C(O)C.[Fe]>[Br:4][C:5]1[C:6]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:7][C:8]([CH3:14])=[C:9]([CH:10]=1)[NH2:11]Iron powder (320 mg, 5.8 mmol) was stirred in ethanol (12 mL) with 1 N HCl solution (0.6 mL, 0.6 mmol) and heated at 60° C. for 2 hours. 5 N aqueous Ammonium chloride solution (1.0 mL, 5.0 mmol) and 4-(2-bromo-5-methyl-4-nitrophenyl)morpholine (350 mg, 1.2 mmol) were added and the mixture was heated at 60° C. for 30 minutes. The mixture was filtered through celite and the collected solids were washed with ethanol. The combined filtrates were evaporated to give the desired compound (0.24 g, 75%). LCMS for C11H16BrN2O (M+H)+: m/z=271.0.
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