alpha,alpha,alpha-Trifluoro-3,5-dinitrotoluene → 5-(Trifluoromethyl)benzene-1,3-diamine

HRID 1912868Notes

Reaction equation

HRID 1912868 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([F:16])([F:15])[F:14])[CH:7]=[C:8]([N+:10]([O-])=O)[CH:9]=1)([O-])=O.[H][H]>C(OCC)(=O)C.CO.[C].[Pd]>[F:14][C:13]([F:15])([F:16])[C:6]1[CH:5]=[C:4]([NH2:1])[CH:9]=[C:8]([NH2:10])[CH:7]=1

Participants

6

Reactant 2

HCID 123060alpha,alpha,alpha-Trifluoro-3,5-dinitrotolueneHCID 178418361HCID 178418361, compound

Product 1

HCID 677815-(Trifluoromethyl)benzene-1,3-diamineYield 101.8%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a mixed solvent of 10 mL of ethyl acetate and 1 mL of methanol, 500 mg (2.12 mmol) of 3,5-dinitrobenzotrifluoride was dissolved, and 20 mg of 10% palladium carbon was added thereto, and the mixture solution was stirred at room temperature for 20 hours in a hydrogen atmosphere at normal pressures. The catalyst was removed by filtration, and the filtrate was concentrated and dried to obtain 380 mg (100%) of a brown oily target product.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customdried

Sources & evidence

ORD record
ord-42835461d1f442a191e953a9b9da28be
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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