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

HRID 1700484Notes

Reaction equation

HRID 1700484 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13](=O)[CH2:12][C:11](=[O:16])[CH2:10]1.C([O-])(=O)C.[NH4+:21]>C(O)C>[NH2:21][C:13]1[CH2:14][CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])[CH2:10][C:11](=[O:16])[CH:12]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 183173185-(2,3-Dichlorophenyl)cyclohexane-1,3-dione

Product 1

HCID 183174461-Amino-5-(2,3-dichlorophenyl)cyclohexen-3-oneYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(2,3-dichlorophenyl)cyclohexane-1,3-dione (1.8 g) and ammonium acetate (1.7 g) in ethanol (20 ml) was refluxed for 14 hours, and the reaction solution was concentrated under reduced pressure. To the residue was added water (20 ml), and the resulting crystals were filtered. The crystals were washed with water and toluene, and dried to give 1-amino-5-(2,3-dichlorophenyl)cyclohexen-3-one (1.6 g) as pale yellow crystals.

Workup

  1. temperaturewas refluxed for 14 hours
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additionTo the residue was added water (20 ml)
  4. filtrationthe resulting crystals were filtered
  5. washThe crystals were washed with water and toluene
  6. customdried

Sources & evidence

ORD record
ord-75975a1469fb4bb790a33048dc41b484
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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