Ammonium Chloride → 1-[4-Amino-3-(trifluoromethyl)phenyl]ethan-1-one

HRID 965955Notes

Reaction equation

HRID 965955 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][C:5]=1[C:13]([F:16])([F:15])[F:14])([O-])=O.[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][C:5]=1[C:13]([F:14])([F:15])[F:16]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 22313797HCID 22313797, compound

Product 1

HCID 223138331-[4-Amino-3-(trifluoromethyl)phenyl]ethan-1-one

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1-[4-nitro-3-(trifluoromethyl)phenyl]-1-ethanone (1.41 g, 6.05 mmol), Fe powder (1.69 g, 30.2 mmol), and NH4Cl (324 mg, 6.05 mmol) in EtOH (24 ml) and water (9 ml) was heated to reflux for 2.5 hours. After cooling to room temperature, the mixture was filtered through a pad of Celite and the filtrate was concentrated. And the residue was dissolved with ethyl acetate (100 ml), washed with water (100 ml), dried-over MgSO4, and concentrated in vacuo to give 1.22 g (quant.) of the title compound as a pale yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2.5 hours
  3. filtrationthe mixture was filtered through a pad of Celite
  4. concentrationthe filtrate was concentrated
  5. dissolutionAnd the residue was dissolved with ethyl acetate (100 ml)
  6. washwashed with water (100 ml), dried-over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5d74cc8b0604d83a503fdb49bbfcc99
Source dataset
uspto-grants-2005_10
Patent number
US06951876B2

Reaction notes

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