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

HRID 484700Notes

Reaction equation

HRID 484700 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. Elementary analysis values as C10H11N3 were as follows.

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-8c7b98bf84ca4a98b8371079d2be445e
Source dataset
uspto-grants-1985_08
Patent number
US04533669

Reaction notes

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