Ammonium Acetate → 3-Amino-5-phenyl-2-cyclohexen-1-one

HRID 1700503Notes

Reaction equation

HRID 1700503 reaction equation
[C:1]1([CH:7]2[CH2:12][C:11](=O)[CH2:10][C:9](=[O:14])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+:19]>C(O)C>[NH2:19][C:11]1[CH2:12][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][C:9](=[O:14])[CH:10]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 5689621,3-Cyclohexanedione, 5-phenyl-

Product 1

HCID 122101053-Amino-5-phenyl-2-cyclohexen-1-oneYield 104.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-phenylcyclohexane-1,3-dione (5.0 g), ammonium acetate (6.1 g) in ethanol (100 ml) was refluxed for 13 hours. Under reduced pressure, the solvent was evaporated, and to the residue were added ethyl acetate and water. Precipitated crystals were filtered, washed with water and dried to give pale yellow crystals of 1-amino-5-phenylcyclohexen-3-one (5.2 g).

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. additionto the residue were added ethyl acetate and water
  3. customPrecipitated crystals
  4. filtrationwere filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-bfa4b366093142eb981d879688d6b71e
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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