[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][CH:9]=1)([O-])=O.C(=O)([O-])[O-].[Na+].[Na+].N>Cl>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][CH:9]=15-Nitro-2-phenoxypyridine (0.5 9, 2.3 mmol) was added portion wise to a solution of stannous chloride (2.6 g, 12 mmol) dissolved in concentrated hydrochloric acid (10 mL) at a temperature of 0-5° C. The reaction mixture was then stirred at 20° C. for 16 hours. Sodium carbonate (5 g) and aqueous ammonia (50 mL) was added. The mixture was extracted with ethyl acetate (2×50 mL) and the combined organic phases were washed with water (2×40 mL), dried (MgSO4), and concentrated in vacuo to give 0.3 g of 5-amino-2-phenoxypyridine.
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