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

HRID 1789478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1789478
[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

Komponenten

5

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8942f05ad9b44f1aa6ee60dbe5607694
Quelldatensatz
uspto-grants-1987_08
Patentnummer
US04689341

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