3-Hydroxy-4-nitrophenyl acetate → 4-Amino-3-hydroxyphenyl acetate

HRID 337359Notes

Reaction equation

HRID 337359 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[C:7]([OH:14])[CH:6]=1)(=[O:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([OH:14])[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 201396903-Hydroxy-4-nitrophenyl acetate

Product 1

HCID 197705154-Amino-3-hydroxyphenyl acetateYield 97.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-hydroxy-4-nitrophenyl acetate (3.0 g) in ethyl acetate (50 mL), 300 mg of palladium/carbon (10%) was added under nitrogen atmosphere. The resulting mixture was stirred under hydrogen atmosphere for 10 h at room temperature. The insoluble material was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by the column chromatography over silica gel using hexane/ethyl acetate(1:1) to give the title compound (2.48 g).

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by the column chromatography over silica gel

Sources & evidence

ORD record
ord-5b6dd432e2124df6b9238f3de8079bad
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Reaction notes

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