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

HRID 2081605Notes

Reaction equation

HRID 2081605 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). In a similar manner there were also prepared:

Workup

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

Sources & evidence

ORD record
ord-ac00b31b79604b238565a8b96c59a582
Source dataset
uspto-grants-1993_02
Patent number
US05185346

Reaction notes

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