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

HRID 1051255Notes

Reaction equation

HRID 1051255 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]>[Pd].CO>[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 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Methyl-2-(3-nitrophenyl)propanenitrile (0.6 g, 3.15 mmol) obtained in Step (1) above was stirred in a solvent of methanol. The reaction solution was mixed with Pd/C (0.06 g, 0.56 mmol), followed by stirring under hydrogen conditions for about 2 hours at room temperature. The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with methanol. The filtrate was concentrated under reduced pressure to obtain the title compound (0.48 g, 95%).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad under reduced pressure
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-66d28f7e373e4562a4edff1cf7542442
Source dataset
uspto-grants-2016_07
Patent number
US09388165B2

Reaction notes

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