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

HRID 1739812Notes

Reaction equation

HRID 1739812 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]>C(O)C.[Ni]>[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 99.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of intermediate (1-a) (39 g) in ethanol (300 ml) was hydrogenated (3.9 105Pa H2) with Raney nickel (20 g) as a catalyst. After uptake of hydrogen (3 equivalents), the catalyst was filtered off and the filtrate was evaporated, yielding 34.6 g of (±)-4-[(1H-imidazol-1-yl)phenylmethyl]benzenamine (interm. 1-b).

Workup

  1. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-6f303531814e4a738fb1cd29cff06cef
Source dataset
uspto-grants-1999_10
Patent number
US05968952

Reaction notes

Loading…