[Cl:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[N:5]=[CH:4][C:3]=1[N+:13]([O-])=O.[Cl-].[NH4+]>C(O)C.[Fe]>[Cl:1][C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[N:5]=[CH:4][C:3]=1[NH2:13]To a solution of 5-chloro-4-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole (0.4 g, 2 mmol) in ethanol (10 mL) was added ammonium chloride (0.3 g, 5 mmol) and iron (0.3 g). The reaction was stirred at 90° C. for 30 minutes before filtered through celite and concentrated. The residue was triturated in EtOAc and filtered. The filtrated was concentrated to give the title compound (0.34 g, quant.)
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