2-Methyl-2-(4-nitrophenyl)propanenitrile → 2-(4-Aminophenyl)-2-methylpropanenitrile

HRID 1663661Notes

Reaction equation

HRID 1663661 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)([CH3:5])[C:3]#[N:4]>C(OCC)(=O)C.[Pd]>[NH2:12][C:9]1[CH:8]=[CH:7][C:6]([C:2]([CH3:5])([CH3:1])[C:3]#[N:4])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 8236152-Methyl-2-(4-nitrophenyl)propanenitrile

Product 1

HCID 100578012-(4-Aminophenyl)-2-methylpropanenitrileYield 101.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-methyl-2-(4-nitrophenyl)propanenitrile (0.95 g, 5.0 mmol) in ethyl acetate (10 mL) was added 10% palladium/carbon (100 mg), and the mixture was stirred at room temperature for 14 hr under hydrogen atmosphere. The residual catalyst was filtered through celite, and washed with ethyl acetate. The filtrate was concentrated under reduced pressure to give the title compound (0.81 g, 99%) as a pale-yellow oil.

Workup

  1. filtrationThe residual catalyst was filtered through celite
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2c1c36e8511f49c6a0c97aa035b15db4
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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