2-Methyl-1-(4-nitrophenyl)-1H-imidazole → 4-(2-methyl-1H-imidazol-1-yl)aniline

HRID 536624Notes

Reaction equation

HRID 536624 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1>CO.[Pd]>[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1

Participants

4

Reactant 1

HCID 100131182-Methyl-1-(4-nitrophenyl)-1H-imidazole

Product 1

HCID 31574784-(2-methyl-1H-imidazol-1-yl)anilineYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution 2-methyl-1-(4-nitrophenyl)-1H-imidazole (12.8 g, 63 mmol) in MeOH (150 mL) was added Pd/C (3 g). The resulting mixture was stirred at room temperature for 8 hours under hydrogen. When TLC indicated the starting material was consumed, the mixture was filtered and concentrated in vacuo to give 4-(2-methyl-1H-imidazol-1-yl)aniline (10 g, yield 92%).

Workup

  1. customwas consumed
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34da12734cf04a3991d44ec1ee338719
Source dataset
uspto-grants-2014_10
Patent number
US08859611B2

Reaction notes

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