Ethyl Acetate → 2-(4-Aminophenyl)-1-(1-propylimidazol-2-yl)ethanone

HRID 856803Notes

Reaction equation

HRID 856803 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([C:13]2[N:14]([CH2:18][CH2:19][CH3:20])[CH:15]=[CH:16][N:17]=2)=[O:12])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[Ca+2].[Cl-].C(OCC)(=O)C>C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([C:13]2[N:14]([CH2:18][CH2:19][CH3:20])[CH:15]=[CH:16][N:17]=2)=[O:12])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 5284359Calcium ChlorideHCID 229386482-(4-Nitrophenyl)-1-(1-propylimidazol-2-yl)ethanone

Product 1

HCID 229387292-(4-Aminophenyl)-1-(1-propylimidazol-2-yl)ethanoneYield 80.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous solution (20 ml) of (2-(4-nitrophenyl)-1-(1-propylimidazol-2-yl)ethanone (1.2 g), reduced iron (1.2 g) and anhydrous calcium chloride (244 mg) in 85% ethanol was stirred for 4 hours under nitrogen atmosphere at 105° C. The mixture was allowed to be at room temperature, ethyl acetate was added to the mixture, the insolubles were filtered off, and water was added to separate the layers. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=0.4:1) to give 2-(4-aminophenyl)-1-(1-propylimidazol-2-yl)ethanone (863 mg) as red oil.

Workup

  1. customto be at room temperature
  2. filtrationthe insolubles were filtered off
  3. additionwater was added
  4. customto separate the layers
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=0.4:1)

Sources & evidence

ORD record
ord-0bdec48eb90844e3a9ee7db862f4d8af
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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