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

HRID 1700696Notes

Reaction equation

HRID 1700696 reaction equation
[F: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[F:1])[CH2:10][C:11](=[O:16])[CH:12]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 183174315-(2-Fluoro-5-methylphenyl)cyclohexane-1,3-dione

Product 1

HCID 183176231-Amino-5-(2-fluoro-5-methylphenyl)cyclohexen-3-oneYield 87.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(2-fluoro-5-methylphenyl)cyclohexane-1,3-dione (1.5 g) and ammonium acetate (1.6 g) in ethanol (23 ml) was refluxed for 20 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-fluoro-5-methylphenyl)cyclohexen-3-one (1.3 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-15bf297343ad43148504d34913f2ae9b
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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