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

HRID 1600412Notes

Reaction equation

HRID 1600412 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([N+:8]([O-])=O)[CH:7]=1.C1C=C(S([O-])(=O)=O)C=C(P(C2C=CC=C(S([O-])(=O)=O)C=2)C2C=CC=C(S([O-])(=O)=O)C=2)C=1.[Na+].[Na+].[Na+].P.[OH-].[Na+]>Cl[Pd]Cl.O.C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:7]=1)[NH2:8]

Participants

8

Reactant 4

HCID 69804-Chloro-2-nitrophenolHCID 14798Sodium HydroxideHCID 24404PhosphineHCID 6099338Trisodium 3,3',3''-phosphinetriyltris(benzene-1-sulphonate)2×

Product 1

HCID 72652-Amino-4-chlorophenol

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 7237O-XyleneSolvent

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).0.25 mmol of TPPTS (in the form of 4.6 g of an aqueous solution containing 0.546 mol of TPPTS/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 to 10.5.

Workup

  1. additionare added

Sources & evidence

ORD record
ord-43d247b102ec4fe68a2033feee667dff
Source dataset
uspto-grants-1998_04
Patent number
US05744643

Reaction notes

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