4-Chloro-2-nitrophenol → 2-Amino-4-chlorophenol

HRID 1600414Notes

Reaction equation

HRID 1600414 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([N+:8]([O-])=O)[CH:7]=1.C1(C)C(C)=CC=CC=1.P.[OH-].[Na+]>Cl[Pd]Cl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:7]=1)[NH2:8]

Participants

7

Reactant 4

HCID 69804-Chloro-2-nitrophenolHCID 7237O-XyleneHCID 14798Sodium HydroxideHCID 24404Phosphine

Product 1

HCID 72652-Amino-4-chlorophenol

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent

Procedure

A degassed solution of 10 mmol of 5-chloro-2-hydroxynitrobenzene (starting material) and 40 ml of xylene are placed in an autoclave (volume: 200 ml).0.125 mmol of ligand A (in the form of 1.25 g of an aqueous solution containing 0.1 mol of ligand A/kg of solution) as phosphine and 0.6 g (15 mmol) of NaOH, 41 ml of H2O and 0.25 mmol of PdCl2 are added. The pH is from 10.5 to 11.0.

Workup

  1. additionare added

Sources & evidence

ORD record
ord-fac790a02d9a4e2aaf843796356f4b6a
Source dataset
uspto-grants-1998_04
Patent number
US05744643

Reaction notes

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