2,6-Dimethyl-4-nitro-4'-(trifluoromethyl)biphenyl → 2,6-Dimethyl-4'-(trifluoromethyl)biphenyl-4-amine

HRID 642803Notes

Reaction equation

HRID 642803 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH3:11])[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1>C(O)C.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:11])[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:21])[F:20])=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 674856592,6-Dimethyl-4-nitro-4'-(trifluoromethyl)biphenyl

Product 1

HCID 674849042,6-Dimethyl-4'-(trifluoromethyl)biphenyl-4-amineYield 103.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2,6-dimethyl-4-nitro-4′-trifluoromethyl-biphenyl (0.68 g) in ethanol (20 mL) is added 10% palladium on carbon (0.02 g). The reaction is charged to 30 psi under a hydrogen atmosphere and allowed to stir for 4 h. The mixture is then filtered through a pad of Celite®. The solution is concentrated and purified by reverse phase HPLC using 0.1% TFA in water and acetonitrile to afford 0.63 g of the titled compound. 1H-NMR.

Workup

  1. additionThe reaction is charged to 30 psi under a hydrogen atmosphere
  2. filtrationThe mixture is then filtered through a pad of Celite®
  3. concentrationThe solution is concentrated
  4. custompurified by reverse phase

Sources & evidence

ORD record
ord-2a30067f54cc4c7489fe7f642c133cb4
Source dataset
uspto-grants-2010_04
Patent number
US07696248B2

Reaction notes

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