O-Xylene → 3-Amino-4-chlorobenzonitrile

HRID 1600411Notes

Reaction equation

HRID 1600411 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-])=O.C1(C)C(C)=CC=CC=1.P.[OH-].[Na+]>Cl[Pd]Cl.O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[NH2:10]

Participants

7

Reactant 4

HCID 7237O-XyleneHCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 14798Sodium HydroxideHCID 24404Phosphine

Product 1

HCID 1044643-Amino-4-chlorobenzonitrile

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent

Procedure

A degassed solution of 40 mmol of 4-chloro-3-nitrobenzonitrile (starting material) and 40 ml of xylene are placed in an autoclave (volume: 200 ml).2.5 mmol of BINAS (in the form of 14.4 g of an aqueous solution containing 0.173 mol of BINAS/kg of solution) as phosphine and 2.4 g (60 mmol) of NaOH, 23.8 ml of H2O and 1.0 mmol of PdCl2 are added. The pH isfrom 10.5 to 11.0.

Workup

  1. additionare added

Sources & evidence

ORD record
ord-67e7033359344b8390da6510655e62d7
Source dataset
uspto-grants-1998_04
Patent number
US05744643

Reaction notes

Loading…