alpha,alpha,alpha-Trifluoro-3-nitro-o-xylene → Trifluoromethyl toluidine

HRID 1762309Notes

Reaction equation

HRID 1762309 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[H][H]>CO.[Pd]>[NH2:8][C:7]1[C:2]([CH3:1])=[C:3]([C:11]([F:12])([F:13])[F:14])[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 81171alpha,alpha,alpha-Trifluoro-3-nitro-o-xyleneHCID 178418361HCID 178418361, compound

Product 1

HCID 2735932Trifluoromethyl toluidineYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-methyl-3-nitrobenzotrifluoride (41.0 g, 0.2 m) in methanol (100 ml) was stirred under an atmosphere of dry nitrogen at room temperature and palladium on charcoal catalyst (10% w/w, 1.0 g) was added. The stirred mixture was warmed to 40°-45° and then hydrogen was passed into the solution at atmospheric pressure until the reduction, as observed by thin-layer chromatography, was complete (4-5 hours). The solution was cooled to room temperature and the catalyst removed by filtration. Distillation of the solvent at atmospheric pressure followed by steam distillation of the crude product gave 3-amino-2-methylbenzotrifluoride (32.2 g, 92% yield), as a pale-brown oil which slowly crystallized.

Workup

  1. temperatureThe stirred mixture was warmed to 40°-45°
  2. custom(4-5 hours)
  3. customthe catalyst removed by filtration
  4. distillationDistillation of the solvent at atmospheric pressure
  5. distillationfollowed by steam distillation of the crude product

Sources & evidence

ORD record
ord-09fda287c2444726b8e8807006589159
Source dataset
uspto-grants-1989_05
Patent number
US04831193

Reaction notes

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