[NH2:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[CH:6][C:5]([C:15]([O:17][CH3:18])=[O:16])=[CH:4][C:3]=1[N+:19]([O-])=O.O.O.[Sn]Cl.[Cl-].[NH4+].O>CN(C)C=O.C(OCC)(=O)C>[NH2:19][C:3]1[CH:4]=[C:5]([C:15]([O:17][CH3:18])=[O:16])[CH:6]=[C:7]([C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)[C:2]=1[NH2:1]
To a solution of methy 6-amino-4′-fluoro-5-nitrobiphenyl-3-carboxylate (0.42 g, 1.44 mmol) in N,N-dimethylformamide (4.8 mL) was added tin(1) chloride dihydrate (1.3 g, 5.8 mmol). The mixture was stirred at ambient temperature for 4 h and stored in the refrigerator for 18 h. Saturated ammonium chloride, water, and ethyl acetate were added. The mixture was extracted with ethyl acetate (3×). The combined organic layer was dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) gave the title compound (0.17 g): LC-MS [M+1]=261.2.
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