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

HRID 1700508Notes

Reaction equation

HRID 1700508 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 refluxed for 12 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give crystals, which were recrystallized from ethyl acetate-hexane to give pale yellow crystals of 1-amino-5-(2-chlorophenyl)cyclohexen-3-one (2.2 g).

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. additionto the residue was added sodium hydrogen carbonate solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with water and saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated
  7. customto give crystals, which
  8. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-84967c8f835046a49600d84a59f2d071
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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