Acetic Anhydride → N-(4-fluoro-2-hydroxyphenyl)acetamide

HRID 270055Notes

Reaction equation

HRID 270055 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([OH:8])[CH:7]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>[Pt].CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:9][C:12](=[O:14])[CH3:13])=[C:6]([OH:8])[CH:7]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 99375-Fluoro-2-nitrophenol

Product 1

HCID 177738N-(4-fluoro-2-hydroxyphenyl)acetamideYield 87.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-fluoro-2-nitrophenol (5 g, 31.8 mmol), acetic anhydride (4.86 g, 47.7 mmol) and platinum on carbon (5%, 200 mg) in methanol was hydrogenated at 35 psi for 3 hours. The catalyst was filtered off and the residue was purified by silica gel flash chromatography to give the subtitled compound (4.7 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-a26a1d68247b4745ab08f78a13da12b9
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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