Water → HCID 18616551, compound

HRID 1594815Notes

Reaction equation

HRID 1594815 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. Th e 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. temperatureTh e 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-3d0bf6dda30c4025b120f850333e65aa
Source dataset
uspto-grants-2001_09
Patent number
US06284764B1

Reaction notes

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