1-(4-Nitrophenyl)-1H-imidazole → 4-(1H-imidazol-1-yl)aniline

HRID 1733869Notes

Reaction equation

HRID 1733869 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1>C(OCC)(=O)C.C(O)C.[Pd]>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 1

HCID 1231551-(4-Nitrophenyl)-1H-imidazole

Product 1

HCID 3201654-(1H-imidazol-1-yl)anilineYield 80%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(1H-imidazol-1-yl)-nitrobenzene (20 g; ~0.11 mol) in a mixture of 500 ml ethyl acetate and 500 ml ethanol was hydrogenated in a Parr hydrogenation apparatus at 28.12 kPa (40 psi) and 25° C. by using 0.5 g 5% Pd-C as a catalyst. The reaction mixture was filtered and evaporated in vacuo to give the title compound (14 g) as crystals. M.p. 142°-144° C.

Workup

  1. customwas hydrogenated in a Parr hydrogenation apparatus at 28.12 kPa (40 psi) and 25° C.
  2. filtrationThe reaction mixture was filtered
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-f137254f1c0346fbaae909fb3dca7450
Source dataset
uspto-grants-1996_07
Patent number
US05532236

Reaction notes

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