5-methyl-1-(4-nitrobenzyl)-1H-imidazole → 1-(4-aminobenzyl)-5-methyl-1H-imidazole

HRID 30695Notes

Reaction equation

HRID 30695 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[CH:5]=[N:4][CH:3]=1>[C].[Pd].C(O)C>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][N:6]2[C:2]([CH3:1])=[CH:3][N:4]=[CH:5]2)=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 4266335-methyl-1-(4-nitrobenzyl)-1H-imidazole

Product 1

HCID 692085411-(4-aminobenzyl)-5-methyl-1H-imidazoleYield 97%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-methyl-1-(4-nitrobenzyl)-1H-imidazole (1.4 g), 10% palladium carbon (200 mg) and ethanol (20 ml) was stirred under a hydrogen atmosphere at room temperature for 4 hrs. Palladium carbon was removed from the reaction mixture by filtration, and the filtrate was concentrated. Recrystallization of the residue from ethyl acetate-hexane gave 1-(4-aminobenzyl)-5-methyl-1H-imidazole (1.17 g, 97%) as colorless prism crystals. melting point: 124-125° C.

Workup

  1. customPalladium carbon was removed from the reaction mixture by filtration
  2. concentrationthe filtrate was concentrated
  3. customRecrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-796834830e984f95906c43c487a8bc70
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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