S(S([O-])=O)([O-])=O.[Na+].[Na+].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([NH:18][C:19](=[O:21])[CH3:20])[CH3:17])=[CH:12][C:11]=1[N+:22]([O-])=O.C([O-])(O)=O.[Na+]>O.CCO>[NH2:22][C:11]1[CH:12]=[C:13]([CH:16]([NH:18][C:19](=[O:21])[CH3:20])[CH3:17])[CH:14]=[CH:15][C:10]=1[Cl:9]A solution of sodium dithionite (1.08 g, 6.1 mmol) in H2O (4 mL) was added to a vigorously stirred mixture of N-[1-(4-chloro-3-nitrophenyl)ethyl]acetamide (0.30 g, 1.2 mmol) in EtOH (20 mL) at 55° C. After 4 h at 55° C. additional sodium dithionite (0.20 g, 1.1 mmol) was added and stirring was continued at 55° C. for 1.5 h. The mixture was allowed to cool and NaHCO3 (aq, sat) was added. The mixture was extracted with EtOAc and the combined extracts were dried over Na2SO4 and concentrated to give the sub-title compound.
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