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

HRID 1995086Notes

Reaction equation

HRID 1995086 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>C(O)C.[Pd]>[NH2:13][C:10]1[CH:9]=[CH:8][C:7]([N:3]2[CH:4]=[CH:5][N:6]=[C:2]2[CH3:1])=[CH:12][CH:11]=1

Participants

4

Reactant 1

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

Product 1

HCID 31574784-(2-methyl-1H-imidazol-1-yl)anilineYield 85.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

13.5 g of 2-methyl-1-(4-nitrophenyl)imidazole was hydrogenated in the presence of 10% Pd/c in 160 ml of ethanol at 30° to 40° C. at an initial pressure of 40 kg/cm2. After 3 hours, the reduction mixture was filtered and the solvent was removed from the filtrate under reduced pressure. The residue was recrystallized from a mixed solvent of benzene and n-hexane to obtain 9.8 g of the intended compound having a melting point of 112° to 113° C.

Workup

  1. filtrationthe reduction mixture was filtered
  2. customthe solvent was removed from the filtrate under reduced pressure
  3. customThe residue was recrystallized from a mixed solvent of benzene and n-hexane

Sources & evidence

ORD record
ord-86203b21db594a2d96a96c951e5470e6
Source dataset
uspto-grants-1983_09
Patent number
US04402966

Reaction notes

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