2,4-Dichloro-6-nitrophenol → 2-Amino-4,6-dichlorophenol

HRID 1732848Notes

Reaction equation

HRID 1732848 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[OH:12].[H][H]>[Pd].C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([NH2:9])[C:3]=1[OH:12]

Participants

5

Reactant 2

HCID 118712,4-Dichloro-6-nitrophenolHCID 178418361HCID 178418361, compound3×

Product 1

HCID 106992-Amino-4,6-dichlorophenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 10 g (0.048 moles) of 2,4-dichloro-6-nitrophenol and 0.2 g of 5% palladium on carbon slurried in 250 ml of glacial acetic acid was placed in a hydrogenation bottle. The bottle was stoppered under an atmosphere of 40 psi hydrogen and shaken at room temperature. The hydrogen was replenished during reaction. After four and one-half hours the hydrogen uptake was complete. The mixture then was filtered through a sintered glass funnel and the filtrate was stripped of solvent under reduced pressure. The yield of product was quantitative.

Workup

  1. filtrationThe mixture then was filtered through a sintered glass funnel

Sources & evidence

ORD record
ord-e5c543f8258945eb980f90fd1326edb8
Source dataset
uspto-grants-1980_12
Patent number
US04239699

Reaction notes

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