Hydrochloric Acid → 4-Methyl-2-(trifluoromethyl)aniline

HRID 579857Notes

Reaction equation

HRID 579857 reaction equation
Cl.O1CCOCC1.[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=1[C:18]([F:21])([F:20])[F:19])([O-])=O>O.[Fe]>[F:19][C:18]([F:20])([F:21])[C:12]1[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:11]=1[NH2:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 134554324-Methyl-1-nitro-2-(trifluoromethyl)benzene

Product 1

HCID 27377104-Methyl-2-(trifluoromethyl)anilineYield 86.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

100 g of iron fillings are heated to 95° C. in 300 ml of water, 5 ml of hydrochloric acid and 5 ml of dioxane in a stirred vessel, and 57 g of 2-nitro-5-methylbenzotrifluoride are added dropwise in the course of about 1 hour. The mixture is stirred for a further 2 hours, and a distillation is then carried out using steam. The organic material extracted with dichloromethane and re-distilled. 42 g (boiling point: 92°-95° C./20 mbar) of 2-trifluoromethyl-4-methylaniline are obtained.

Workup

  1. distillationa distillation
  2. extractionThe organic material extracted with dichloromethane
  3. distillationre-distilled

Sources & evidence

ORD record
ord-803b3e8da6c14466a4316cba997ef9ae
Source dataset
uspto-grants-1988_06
Patent number
US04749813

Reaction notes

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