[1-(4-nitrobenzyl)-1H-imidazol-2-yl]methanol → HCID 69208976, compound

HRID 30693Notes

Reaction equation

HRID 30693 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[CH2:14][OH:15])=[CH:6][CH:5]=1)([O-])=O>[C].[Pd].C(O)C>[NH2:1][C:4]1[CH:17]=[CH:16][C:7]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[CH2:14][OH:15])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 15079328[1-(4-nitrobenzyl)-1H-imidazol-2-yl]methanol

Product 1

HCID 69208976HCID 69208976, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of [1-(4-nitrobenzyl)-1H-imidazol-2-yl]methanol (3.6 g), 10% palladium carbon (400 mg) and ethanol (50 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)-1H-imidazol-2-yl]methanol (2.53 g, 95%) as colorless prism crystals. melting point: 125° C. (decomposition)

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-88fab999df784d1f9a32cb40afeafe81
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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