[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([N+:11]([O-])=O)[CH:5]=1)=[O:3].O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O.O>[NH2:11][C:6]1[CH:5]=[C:4]([C:2](=[O:3])[CH3:1])[CH:9]=[CH:8][C:7]=1[NH2:10]To a solution of 4-methylcarbonyl-2-nitro-benzenamine (500 mg, 2.775 mmol) in EtOAc (16 mL) was added SnCl2.2H2O (3.130 g, 13.88 mmol). The reaction mixture was refluxed for 2.5 h, cooled to rt, and diluted with H2O (130 mL). The pH of the mixture was adjusted to 7-8 by addition of saturated NaHCO3 solution and the aqueous phase was extracted with EtOAc (2×120 mL). The combined organic extracts were washed with brine (2×60 mL) and dried over MgSO4. After the removal of the solvent under vacuum, 142a was obtained as a red orange solid (418 mg).
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