Calcium Chloride → 4-[2-(1H-Imidazol-1-yl)ethoxy]aniline

HRID 856724Notes

Reaction equation

HRID 856724 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[Ca+2].[Cl-]>C(O)C>[N:11]1([CH2:10][CH2:9][O:8][C:7]2[CH:16]=[CH:17][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

4

Reactant 2

HCID 5284359Calcium ChlorideHCID 135691861-(2-(P-NO2Phenoxy)ethyl)imidazole

Product 1

HCID 135692034-[2-(1H-Imidazol-1-yl)ethoxy]anilineYield 55.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1-[2-(4-nitrophenoxy)ethyl]imidazole (0.64 g) was added 85% ethanol solution (19.2 ml), calcium chloride (0.15 g) and reduced iron (0.77 g) were added to the mixture, and the mixture was heated to reflux for 3 hours. After cooling to room temperature, the mixture was filtered with. Celite, and washed with ethyl acetate. The solvent was removed under reduced pressure, and the obtained residue was dissolved in ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 4-[2-(imidazol-1-yl)ethoxy]aniline (0.31 g).

Workup

  1. additionwere added to the mixture
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 3 hours
  4. filtrationthe mixture was filtered with
  5. washCelite, and washed with ethyl acetate
  6. customThe solvent was removed under reduced pressure
  7. dissolutionthe obtained residue was dissolved in ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was removed under reduced pressure
  11. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4d105b04526c421aac613ab7921dc257
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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