Hydrochloric Acid → 4-Chloro-2-methyl-3-(trifluoromethyl)aniline

HRID 723707Notes

Reaction equation

HRID 723707 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)C(C)(C)C)=[C:4]([CH3:15])[C:3]=1[C:16]([F:19])([F:18])[F:17].Cl>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH3:15])[C:3]=1[C:16]([F:17])([F:18])[F:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21874848N-[4-chloro-2-methyl-3-(trifluoromethyl)phenyl]-2,2-dimethylpropanamide

Product 1

HCID 179957894-Chloro-2-methyl-3-(trifluoromethyl)anilineYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(4-Chloro-2-methyl-3-trifluoromethylphenyl)-2,2-dimethyl-propionamide 1.0 g, 3.4 mmol) was added to a 1:1 mixture (15 mL) of concentrated HCl and ethanol and heated at reflux for overnight. The reaction was cooled and concentrated in vacuo to give a tan solid which was then partitioned between EtOAc and saturated NaHCO3. The organic layer was separated, washed with water, brine, dried (Na2SO4), filtered and concentrated to give compound 760C (0.54g, 76%) as a brown oily solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for overnight
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated in vacuo
  5. customto give a tan solid which
  6. customwas then partitioned between EtOAc and saturated NaHCO3
  7. customThe organic layer was separated
  8. washwashed with water, brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-e79b05be6b1746ca8edb2186708f812d
Source dataset
uspto-grants-2006_11
Patent number
US07141578B2

Reaction notes

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