Ammonium Acetate → 1-Amino-5-(5-chloro-2-fluorophenyl)cyclohexan-3-one

HRID 1700702Notes

Reaction equation

HRID 1700702 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([CH:8]2[CH2:13][C:12](=O)[CH2:11][C:10](=[O:15])[CH2:9]2)[CH:7]=1.C([O-])(=O)C.[NH4+:21]>C(O)C>[NH2:21][CH:12]1[CH2:13][CH:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[F:16])[CH2:9][C:10](=[O:15])[CH2:11]1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 183175245-(5-Chloro-2-fluorophenyl)cyclohexane-1,3-dione

Product 1

HCID 183173031-Amino-5-(5-chloro-2-fluorophenyl)cyclohexan-3-oneYield 72.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(5-chloro-2-fluorophenyl)cyclohexane-1,3-dione (2 g) and ammonium acetate (1.9 g) in ethanol (15 ml) was refluxed for 15 hours. The reaction solution was concentrated under reduced pressure, and to the residue were added water (30 ml) and ethyl acetate (150 ml). The mixture was shaken, and the separated upper layer was washed with water and concentrated under reduced pressure. The residue was washed with ethyl acetate and dried to give 1-amino-5-(5-chloro-2-fluorophenyl)cyclohexan-3-one (1.45 g) as yellow crystals.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionto the residue were added water (30 ml) and ethyl acetate (150 ml)
  3. washthe separated upper layer was washed with water
  4. concentrationconcentrated under reduced pressure
  5. washThe residue was washed with ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-72ae725777ab457b997cae867f223b74
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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