1-(3-nitrophenyl)benzimidazole → 3-(1H-Benzo[d]imidazol-1-yl)aniline

HRID 1603845Notes

Reaction equation

HRID 1603845 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]=[CH:11]2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]=[CH:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 53284431-(3-nitrophenyl)benzimidazole

Product 1

HCID 53284443-(1H-Benzo[d]imidazol-1-yl)anilineYield 71%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Reduction of 1-(3-nitrophenyl)benzimidazole (prepared by the method of M. A. Khan and J. B. Polya, J. Chem. Soc. (C), 1970: 85-91) with Raney nickel as for Example 8, followed by chromatography on silica gel, eluting with EtOAc, gave Example 3 (71%) mp (EtOAc/hexane) 93-95° C.

Workup

  1. washeluting with EtOAc

Sources & evidence

ORD record
ord-fe1784c53b7142688420b6f3d907aa15
Source dataset
uspto-grants-1999_11
Patent number
US05990146

Reaction notes

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