1,1'-Biphenyl, 4-(1,1-dimethylethyl)-4'-nitro- → 4'-(1,1-Dimethylethyl)[1,1'-biphenyl]-4-amine

HRID 642801Notes

Reaction equation

HRID 642801 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 30259791,1'-Biphenyl, 4-(1,1-dimethylethyl)-4'-nitro-

Product 1

HCID 201001574'-(1,1-Dimethylethyl)[1,1'-biphenyl]-4-amineYield 100.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the 4′-tert-Butyl-4-nitro-biphenyl (1.8 g) in ethanol (20 mL) is added palladium (10%) on carbon (0.15 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 1.6 g of the titled compound as a white solid. 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-b486753944404331a6198e295cf50df9
Source dataset
uspto-grants-2010_04
Patent number
US07696248B2

Reaction notes

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