3,6-Dichloro-2-nitrophenol → 2-amino-3,6-dichloroPhenol

HRID 1033031Notes

Reaction equation

HRID 1033031 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([N+:9]([O-])=O)[C:3]=1[OH:12]>C(O)C.C(O)(=O)C.[Pt]>[NH2:9][C:4]1[C:5]([Cl:8])=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[OH:12]

Participants

5

Reactant 1

HCID 30141723,6-Dichloro-2-nitrophenol

Product 1

HCID 103973432-amino-3,6-dichloroPhenolYield 100%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A yellow solution of 2,5-dichloro-6-nitrophenol (10.0 g, 48.0 mmol) in ethanol (200 mL) and acetic acid (13.8 mL) at 0° C. was catalytically reduced in the presence of 5% Platinum on charcoal (0.15 g) under an atmosphere of hydrogen (25 psi) for 1 hour in a Parr hydrogenator. The resultant colorless solution was filtered and concentrated under reduced pressure (15 torr). The residue was then dried under high vacuum (0.02 torr) overnight to yield 8.52 g (100%) of 2-amino-3,6-dichlorophenol.

Workup

  1. filtrationThe resultant colorless solution was filtered
  2. concentrationconcentrated under reduced pressure (15 torr)
  3. customThe residue was then dried under high vacuum (0.02 torr) overnight

Sources & evidence

ORD record
ord-8ed0c95016094406819391c7adda635e
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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