1-[(4-Nitrophenyl)(phenyl)methyl]-1H-imidazole → 4-((1H-Imidazol-1-yl)(phenyl)methyl)aniline

HRID 1756521Notes

Reaction equation

HRID 1756521 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Ni].C(O)C>[N:11]1([CH:10]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

5

Reactant 2

HCID 141740671-[(4-Nitrophenyl)(phenyl)methyl]-1H-imidazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 141740694-((1H-Imidazol-1-yl)(phenyl)methyl)anilineYield 99.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 39 parts of intermediate 42, namely 1-[(4-nitrophenyl)phenylmethyl]-1H-imidazole, in 240 parts of ethanol was hydrogenated at 3.105Pa and at room temperature with 20 parts of Raney nickel. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated, yielding 34.6 parts (99.1%) of 4-[(1H-imidazol-1-yl)phenylmethyl]-benzenamine (interm. 43).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-b2d56fa542ea48e2acc34660ef4e6c58
Source dataset
uspto-grants-1995_08
Patent number
US05441954

Reaction notes

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