1-methyl-2-[(2-nitrophenoxy)methyl]-1H-imidazole → 1-methyl-2-[(2-aminophenoxy)methyl]-1H-imidazole

HRID 983356Notes

Reaction equation

HRID 983356 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-])=O>CO.[Pd]>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15]

Participants

4

Reactant 1

HCID 225596511-methyl-2-[(2-nitrophenoxy)methyl]-1H-imidazole

Product 1

HCID 225594921-methyl-2-[(2-aminophenoxy)methyl]-1H-imidazoleYield 86.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.13 g of 1-methyl-2-[(2-nitrophenoxy)methyl]-1H-imidazole in 70 ml of methanol with 0.14 g of palladium on charcoal 10% was hydrogenated at 50 psi for 6 hours at room temperature. The catalyst was then separated by filtration and the solvent evaporated. The residue was finally purified by chromatography on a silica gel column (eluent: chloroform-methanol 48/2) giving rise 0.856 g of the title compound as a red oil.

Workup

  1. customThe catalyst was then separated by filtration
  2. customthe solvent evaporated
  3. customThe residue was finally purified by chromatography on a silica gel column (eluent: chloroform-methanol 48/2)

Sources & evidence

ORD record
ord-d39177f9c8d54818915ba9468d6c390c
Source dataset
uspto-grants-2005_03
Patent number
US06863647B2

Reaction notes

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