[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=1)([O-])=O.[OH-].[Na+]>CCOC(C)=O>[C:9]1([N:6]2[CH:7]=[CH:8][C:4]([NH2:1])=[CH:5]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1A mixture of 3-nitro-1-phenyl-1H-pyrrole (410 mg, 2.18 mmol) and SnCL2 dihydrate (2.00 g, 8.86 mmol) in EtOAc (15 mL) was stirred at 80 C for 3 h. Aqueous 1N NaOH was added to bring pH to 12. The mixture was filtered through celite. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 1-phenyl-1H-pyrrol-3-amine as a solid (323 mg).
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