N#N.[CH3:3][C:4]1([C:9]2[S:13][CH:12]=[C:11]([CH2:14][N:15]3[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[N:16]3)[CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:3][C:4]1([C:9]2[S:13][CH:12]=[C:11]([CH2:14][N:15]3[CH:19]=[C:18]([NH2:20])[CH:17]=[N:16]3)[CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 1-[5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-3-ylmethyl]-4-nitro-1H-pyrazole (220 mg, 0.75 mmol), iron powder (126 mg, 2.24 mmol) and NH4Cl (201 mg, 3.73 mmol) in a mixture of EtOH (4.0 mL) and water (2.0 mL) was stirred at 75° C. for 30 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (25 mL) was added followed by 1M NaOH (25 mL). The aq. layer was extracted with CH2Cl2 (2×25 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a red oil. LC-MS-conditions 02: tR=0.63 min; [M+H]+=266.09.
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