[Br:1][C:2]1[CH:3]=[C:4]([N+:11]([O-])=O)[C:5]([O:8][CH2:9][CH3:10])=[N:6][CH:7]=1.[Cl-].[NH4+].O>CCO.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]([O:8][CH2:9][CH3:10])=[N:6][CH:7]=15-Bromo-2-ethoxy-3-nitropyridine (805 mg, 3.26 mmol), ammonium chloride (732 mg, 13.68 mmol) and powdered iron (764 mg, 13.68 mmol) were suspended in EtOH (3.4 ml) and water (3.4 ml) and stirred for 90 min at 100° C. The reaction mixture was filtered through Celite after dilution with EtOH. The solvent was evaporated under reduced pressure, water was added and the mixture neutralised to pH=6 with sodium carbonate and extracted with dichloromethane (×3). The organic phase was washed successively with water and brine, dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure. 708 mg (83% yield, 92% purity) of the titled compound were obtained and used in the next synthetic step without further purification.
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