Ammonium Acetate → HCID 18317314, compound

HRID 1700486Notes

Reaction equation

HRID 1700486 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[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[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])[CH2:10][C:11](=[O:16])[CH:12]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 6080245-(2,6-Dichlorophenyl)cyclohexane-1,3-dione

Product 1

HCID 18317314HCID 18317314, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(2,6-dichlorophenyl)cyclohexane-1,3-dione (1.8 g) and ammonium acetate (1.7 g) in ethanol (20 ml) was refluxed for 60 hours, and the reaction solution was concentrated under reduced pressure. To the residue were added ethyl acetate (80 ml) and water (20 ml), and the mixture was shaken and separated. The ethyl acetate layer was washed with water (10 ml, thrice) and concentrated under reduced pressure. To the residue was added ethyl acetate (8 ml) to precipitate crystals, which were filtered and dried to give 1-amino-5-(2,6-dichlorophenyl)cyclohexen-3-one (1.43 g) as pale yellow crystals.

Workup

  1. temperaturewas refluxed for 60 hours
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additionTo the residue were added ethyl acetate (80 ml) and water (20 ml)
  4. customseparated
  5. washThe ethyl acetate layer was washed with water (10 ml, thrice)
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue was added ethyl acetate (8 ml)
  8. customto precipitate crystals, which
  9. filtrationwere filtered
  10. customdried

Sources & evidence

ORD record
ord-3e5de87ed04e40fab6014047b05970d6
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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