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

HRID 2391156Notes

Reaction equation

HRID 2391156 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-99ea68ded1db490d88aea16a16e7e220
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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