Water → HCID 18616551, compound

HRID 1264033Notes

Reaction equation

HRID 1264033 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.[BH4-].[Na+].[Al+3].[Cl-].[Cl-].[Cl-].O>C1COCC1>[CH2:8]([C:6]1[CH:7]=[C:2]([NH2:1])[CH:3]=[CH:4][C:5]=1[O:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 6451240Aluminum(III) ChlorideHCID 18616508HCID 18616508, compound

Product 1

HCID 18616551HCID 18616551, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(5-amino-2-phenoxy-phenyl)-ethanone (0.5 g, 2.20 mmol) in THF (15 ml) was added sodium borohydride(0.4 g, 10.5 mmol) and AlCl3 (anhydrous) (0.803 g, 6.02 mmol) under nitrogen. The resulting reaction mixture was heated under reflux for 4 hours. The mixture was then cooled and iced-water added. The resultant mixture was extracted with EtOAc and dried over Na2SO4. Removal of the solvent afforded a brownish residue which was chromatographed with 4:1 hexane/EtOAc to afford (15 mg, 10%) product 3-ethyl-4-phenoxy-phenylamine.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 4 hours
  4. temperatureThe mixture was then cooled
  5. extractionThe resultant mixture was extracted with EtOAc
  6. dry with materialdried over Na2SO4
  7. customRemoval of the solvent
  8. customafforded a brownish residue which
  9. customwas chromatographed with 4:1 hexane/EtOAc

Sources & evidence

ORD record
ord-ffa1c97af138452591112257ca32d7af
Source dataset
uspto-grants-2003_04
Patent number
US06541481B2

Reaction notes

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