O.[Sn](Cl)Cl.[Cl:5][C:6]1[CH:14]=[C:13]([Cl:15])[C:12]([N+:16]([O-])=O)=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].C([O-])(O)=O.[Na+].CC(O)=O>CCO>[Cl:5][C:6]1[CH:14]=[C:13]([Cl:15])[C:12]([NH2:16])=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]Tin(II) Chloride hydrate (50 g, 0.29 mol) was added to a solution of 2,4-dichloro-5-nitrobenzoic acid 1-2 (10.0 g, 0.045 mol) in EtOH (200 mL). The mixture was stirred for 70° C. for 30 min, cooled and poured onto ice. The pH of the mixture was adjusted to 8 using saturated aqueous NaHCO3. The suspension was left to stir at room temperature for 5 h and re-acidified to pH 5 with glacial AcOH. The resulting white suspension was continuously washed with EtOAc, the extracts combined, washed with brine, dried over Na2SO4, filtered and concentrated to afford the desired amine 1-3 as an off-white solid (8.8 g, 96%). 1H NMR (400 MHz, CD3OD) δ7.27 (s, 1H), 7.30 (s, 1H).
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