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

HRID 1700694Notes

Reaction equation

HRID 1700694 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[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]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=2[Cl:1])[CH2:10][C:11](=[O:16])[CH:12]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 183175785-(2-Chloro-5-methylphenyl)cyclohexane-1,3-dione

Product 1

HCID 183176491-Amino-5-(2-chloro-5-methylphenyl)cyclohexen-3-oneYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(2-chloro-5-methylphenyl)cyclohexane-1,3-dione (3.0 g) and ammonium acetate (2.9 g) in ethanol (50 ml) was refluxed for 13 hours. Under reduced pressure, the solvent was evaporated, and precipitated crystals were washed with water and toluene, and dried to give 1-amino-5-(2-chloro-5-methylphenyl)cyclohexen-3-one (2.9 g).

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. customprecipitated crystals
  3. washwere washed with water and toluene
  4. customdried

Sources & evidence

ORD record
ord-a742a373b9f042bfab59365a24c1a2f3
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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