1-Nitro-2,5-bis(trifluoromethyl)benzene → 2,5-Bis(trifluoromethyl)aniline

HRID 585334

Reaction equation

HRID 585334 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[N+:13]([O-])=O.[H][H]>[Ni].C(O)(C)C>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:10])([F:12])[F:11])=[CH:5][C:4]=1[NH2:13]

Participants

5

Reactant 2

HCID 27340481-Nitro-2,5-bis(trifluoromethyl)benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 7198182,5-Bis(trifluoromethyl)anilineYield 73%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

Into an autoclave, 1.05 g of Raney Nickel catalyst (10 wt %) and 100 ml of isopropanol were introduced, and 10.0 g of 2,5-bis(trifluoromethyl)nitrobenzene was added thereto in small amounts. Hydrogen gas was blown until 5 kg/cm2 with stirring, and the temperature was increased to 70° C. Reaction was carried out at from 70 to 90° C. for 8 hours. After the temperature was recovered to room temperature, hydrogen gas was evacuated, and the Raney Nickel was subjected to filtration and washed with isopropanol. The solvent was concentrated to obtain 2,5-bis(trifluoromethyl)aniline (6.42 g, yield 73%, purity by GC 99.4%). As a result of analysis by GC-Mass, 1H-NMR and 19F-NMR, the product was confirmed to be 2,5-bis(trifluoromethyl)aniline.

Workup

  1. customReaction
  2. customAfter the temperature was recovered to room temperature
  3. customhydrogen gas was evacuated
  4. filtrationthe Raney Nickel was subjected to filtration
  5. washwashed with isopropanol
  6. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-8eb358c7da34435c913e5460880d5ac0
Source dataset
uspto-grants-2005_08
Patent number
US06930214B2

Linked notes

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