[Cl-].[NH4+].[CH3:3][O:4][C:5]([NH:7][C:8]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:9]=1[CH2:10][O:11][C:12]1[C:13]([N+:18]([O-])=O)=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:6]>O.C(O)C.[Fe]>[NH2:18][C:13]1[C:12]([O:11][CH2:10][C:9]2[C:21]([CH3:25])=[CH:22][CH:23]=[CH:24][C:8]=2[NH:7][C:5]([O:4][CH3:3])=[O:6])=[CH:17][CH:16]=[CH:15][N:14]=1To a mixture of iron powder (2.76 g) and ammonium chloride (0.275 g) in water (19 ml) and ethanol (63 ml) was added portionwise 3-(2-methoxycarbonylamino-6-methylbenzyloxy)-2-nitropyridine (6.27 g) under reflux and then stirred for an additional 30 minutes. The hot mixture was filtered by suction and the filtrate was made alkaline with sodium bicarbonate and evaporated in vacuo. The residue was washed with water, dried, and recrystallized from ethyl acetate to give 2-amino-3-(2-methoxycarbonylamino-6-methylbenzyloxy)pyridine.
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