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

HRID 2203262Notes

Reaction equation

HRID 2203262 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].[H][H]>[Pd].C(OCC)(=O)C>[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

5

Reactant 2

HCID 8236152-Methyl-2-(4-nitrophenyl)propanenitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 100578012-(4-Aminophenyl)-2-methylpropanenitrileYield 92.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-methyl-2-(4-nitrophenyl) propanenitrile (4.5 g, 23.6 mmol) was added to a reaction vessel, to which were successively added Pd/C (450 mg) and 50 mL ethyl acetate. The system was vacuumed and hydrogen was introduced. The resulting mixture is reacted at room temperature for 15 hrs. The resulting reaction was filtered with Celite, and washed with ethyl acetate. The resulting filtrate was concentrated to obtain a colorless oil of 2-(4-aminophenyl)-2-methyl propanenitrile (3.5 g).

Workup

  1. customThe resulting mixture is reacted at room temperature for 15 hrs
  2. customThe resulting reaction
  3. filtrationwas filtered with Celite
  4. washwashed with ethyl acetate
  5. concentrationThe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-fd6c323f37f143019fb5bc5299c80537
Source dataset
uspto-grants-2016_06
Patent number
US09365572B2

Reaction notes

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