Acetic Anhydride → 2-Acetylamino-6-fluorophenol

HRID 440235Notes

Reaction equation

HRID 440235 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[OH:11].[C:12](OC(=O)C)(=[O:14])[CH3:13].[H][H]>C(O)(=O)C.[C].[Pd]>[C:12]([NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[OH:11])(=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 737102-Fluoro-6-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 214733642-Acetylamino-6-fluorophenolYield 91.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

In 290 ml of acetic acid were dissolved 26.4 g (0.168 mole) of 2-fluoro-6-nitrophenol and 17.2 g (0.168 mole) of acetic anhydride, and 3.0 g of 5 % palladium carbon was added thereto. Hydrogen gas was passed through the mixture, with stirring, at room temperature for 2 hours. After the reaction mixture had been filtered and the filtrate concentrated under reduced pressure, the residue was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was applied to silica gel column chromatography (the eluent used was a mixture of ethyl acetate : toluene = 1 : 2) to obtain 25.9 g of 2-acetylamino-6-fluorophenol as brown crystals.

Workup

  1. additionwas added
  2. filtrationAfter the reaction mixture had been filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. additiona mixture of ethyl acetate

Sources & evidence

ORD record
ord-791e1b968c4c4026bd31a091a53b686b
Source dataset
uspto-grants-1996_05
Patent number
US05519016

Reaction notes

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