1-[(3-Nitrophenyl)methyl]-1H-imidazole → 3-(1H-Imidazol-1-ylmethyl)aniline

HRID 1388513Notes

Reaction equation

HRID 1388513 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:13]=[CH:14][CH:15]=1)[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:13]=[CH:14][CH:15]=1)[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

4

Reactant 1

HCID 53056321-[(3-Nitrophenyl)methyl]-1H-imidazole

Product 1

HCID 64818213-(1H-Imidazol-1-ylmethyl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(3-nitrobenzyl)imidazole (0.5 g, 0.0025 mol) and palladium on charcoal (0.05 g, 10%) in dry ethanol (20 ml) was stirred under an atmosphere of hydrogen for 0.25 h. The reaction mixture was then filtered through Hyflo-supercel, and the ethanol was evaporated under reduced pressure to give a colourless oil. The oil was distilled to yield 1-(3-aminobenzyl)imidazole, b.p. 160°/0.01 mm Hg, which solidified on cooling. Recrystallisation of the solid from toluene gave the product as a white solid, m.p. 75°-76°.

Workup

  1. filtrationThe reaction mixture was then filtered through Hyflo-supercel
  2. customthe ethanol was evaporated under reduced pressure
  3. customto give a colourless oil
  4. distillationThe oil was distilled

Sources & evidence

ORD record
ord-0735eb4ffb7c4cecaf4532ffa6320444
Source dataset
uspto-grants-1984_02
Patent number
US04431815

Reaction notes

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