1-(4-nitrophenethyl)-1H-imidazole → 4-[2-(1H-imidazol-1-yl)ethyl]aniline

HRID 65255Notes

Reaction equation

HRID 65255 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.Cl.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 33171661-(4-nitrophenethyl)-1H-imidazole

Product 1

HCID 35236744-[2-(1H-imidazol-1-yl)ethyl]aniline

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 10 g (0.046 mole) of 1-[2-(4-nitrophenyl)ethyl]-1H-imidazole in 100 mL of ethanol, 50 mL of 10% aqueous hydrochloric acid and 1.0 g of 5% Pd/C catalyst are placed in a small Parr bottle and hydrogenated at 50 psi pressure for about 24 hours. Additional H2 is added as needed to maintain 50 psi pressure. The reaction mixture is filtered and the solvent is concentrated in vacuo. The residue is dissolved in 100 mL of water and made basic (pH 9) with potassium carbonate. Extract the aqueous mixture with methylene chloride (2×100 mL) and combine. Evaporation of the solvent yields the title compound.

Workup

  1. additionAdditional H2 is added
  2. temperatureto maintain 50 psi pressure
  3. filtrationThe reaction mixture is filtered
  4. concentrationthe solvent is concentrated in vacuo
  5. dissolutionThe residue is dissolved in 100 mL of water
  6. extractionExtract the aqueous mixture with methylene chloride (2×100 mL)
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-923753305b12452b8914bbf6d6af1a3e
Source dataset
uspto-grants-1986_09
Patent number
US04613609

Reaction notes

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