O-Xylene → 3-Aminostyrene

HRID 1600415Notes

Reaction equation

HRID 1600415 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[CH2:8])([O-])=O.C1(C)C(C)=CC=CC=1.P.[OH-].[Na+]>Cl[Pd]Cl.O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[CH2:8]

Participants

7

Reactant 4

HCID 7237O-XyleneHCID 14798Sodium HydroxideHCID 24404PhosphineHCID 685143-Nitrostyrene

Product 1

HCID 42600413-Aminostyrene

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent

Procedure

A degassed solution of 40 mmol of 3-nitrostyrene (starting material) and 40ml of xylene are placed in an autoclave (volume: 200 ml). 2.0 mmol of BINAS(in the form of 11.56 g of an aqueous solution containing 0.173 mol of BINAS/kg of solution) as phosphine and 1.92 g (48 mmol) of NaOH, 23 ml of H2O and 0.8 mmol of PdCl2 are added. The pH is from 10.0 to 10.5.

Workup

  1. additionare added

Sources & evidence

ORD record
ord-9bece42ad5474474b3c3810d974465d3
Source dataset
uspto-grants-1998_04
Patent number
US05744643

Reaction notes

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