Sodium Hydroxide → 2-(Trifluoromethyl)aniline

HRID 2397599Notes

Reaction equation

HRID 2397599 reaction equation
C([O-])=O.[Na+].[OH-].[Na+].Cl[C:8]1[CH:9]=[CH:10][C:11]([NH2:18])=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1>O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[Pd]>[NH2:18][C:11]1[CH:10]=[CH:9][CH:8]=[CH:13][C:12]=1[C:14]([F:15])([F:16])[F:17]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 67961Benzenamine, 4-chloro-2-(trifluoromethyl)-HCID 2723810Sodium Formate

Product 1

HCID 69222-(Trifluoromethyl)anilineYield 60.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

To a solution of sodium formate (38 parts) in water (100 parts) are added sodium hydroxide liquor (32%; 13.5 parts), benzyl triethylammonium chloride (1.0 parts), 3% palladium on charcoal (50% paste; 6.0 parts) and 5-chloro-2-aminobenzotrifluoride (19.6 parts). The mixture is stirred rapidly at the boil under reflux for 4 hours and then steam distilled. The distillate is extracted with chloroform (2 × 50 parts), the extract dried over magnesium sulphate and then the solvent removed to give 9.7 parts (60.3%) of 2-aminobenzotrifluoride.

Workup

  1. temperatureunder reflux for 4 hours
  2. distillationsteam distilled
  3. extractionThe distillate is extracted with chloroform (2 × 50 parts)
  4. dry with materialthe extract dried over magnesium sulphate
  5. customthe solvent removed

Sources & evidence

ORD record
ord-6db2385b03834cebaa75c63e6aed437e
Source dataset
uspto-grants-1977_05
Patent number
US04022795

Reaction notes

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