2-Methyl-2-(3-nitrophenyl)propanenitrile → 2-(3-Aminophenyl)-2-methylpropanenitrile

HRID 1663660Notes

Reaction equation

HRID 1663660 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[CH:7]=1)([CH3:5])[C:3]#[N:4]>C(OCC)(=O)C.[Pd]>[NH2:12][C:8]1[CH:7]=[C:6]([C:2]([CH3:5])([CH3:1])[C:3]#[N:4])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 155413242-Methyl-2-(3-nitrophenyl)propanenitrile

Product 1

HCID 569657872-(3-Aminophenyl)-2-methylpropanenitrileYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-methyl-2-(3-nitrophenyl)propanenitrile (0.35 g, 1.8 mmol) in ethyl acetate (10 mL) was added 10% palladium/carbon (35 mg), and the mixture was stirred for 10 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 (0.35 g, 1.8 mmol) 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-bf55956fdf6149d3a25fa68627269d04
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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