Ammonium Acetate → 1-Amino-5-(2-chlorophenyl)cyclohexen-3-one

HRID 49184Notes

Reaction equation

HRID 49184 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=O)[CH2:11][C:10](=[O:15])[CH2:9]1.C([O-])(=O)C.[NH4+:20]>C(O)C>[NH2:20][C:12]1[CH2:13][CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH2:9][C:10](=[O:15])[CH:11]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 8753605-(2-Chlorophenyl)cyclohexane-1,3-dione

Product 1

HCID 98593161-Amino-5-(2-chlorophenyl)cyclohexen-3-oneYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(2-chlorophenyl)cyclohexane-1,3-dione (2.5 g) and ammonium acetate (2.6 g) in ethanol (50 ml) was heated under reflux for 12 hours. The solvent was distilled off under reduced pressure, and aqueous sodium hydrogen carbonate was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the resultant crystal was recrystallized from ethyl acetate-hexane to obtain 1-amino-5-(2-chlorophenyl)cyclohexen-3-one (2.2 g) as a pale yellow crystal.

Workup

  1. temperatureunder reflux for 12 hours
  2. distillationThe solvent was distilled off under reduced pressure, and aqueous sodium hydrogen carbonate
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resultant crystal was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-96dab39bf17347dea3564a55d20979c8
Source dataset
uspto-grants-2004_03
Patent number
US06706732B1

Reaction notes

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