[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[Cl-].[NH4+].C(O)C.O>CCOCC.[Fe]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:19][CH:18]=2)=[N:10][CH:11]=1A mixture of 2-(4-chlorophenethoxy)-5-nitropyridine (1 g), ammonium chloride (1.9 g), ethanol (40 ml) and water (20 ml) is heated to 70° and then iron powder (1 g), under nitrogen, is added in small portions over about 15 minutes. Heating is continued about 2 hours after the addition of iron is complete. The reaction is cooled and stripped. The residue is taken up in ether, washed with water, dried and solvent evaporated to give 5-amino-2-(4-chlorophenethoxy)pyridine.
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