2-(4-Nitrophenyl)propanenitrile → 2-(4-Aminophenyl)propiononitrile

HRID 660351Notes

Reaction equation

HRID 660351 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:13])[C:11]#[N:12])=[CH:6][CH:5]=1)([O-])=O>[C].[Pd].C1COCC1.CCO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH3:13])[C:11]#[N:12])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 30165492-(4-Nitrophenyl)propanenitrile

Product 1

HCID 1200112-(4-Aminophenyl)propiononitrile

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To the flask was added THF/EtOH (1:1, 70 mL) followed by 2-(4-nitrophenyl)-propionitrile (13.2 g, 74.9 mmol) and 10% palladium carbon (1.07 g) at room temperature. The reaction mixture was hydrogenated and stirred for 30 minutes at 47 psi to 28 psi then filtered through celite bed, and washed with EtOAc. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:3) as eluant.

Workup

  1. filtrationthen filtered through celite bed
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-22174395b9b44522b5d27eb1656ec346
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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