Water → N-(3-Fluorophenyl)acetamide

HRID 1419642Notes

Reaction equation

HRID 1419642 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[F:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12].O>C(O)(=O)C>[CH3:6][C:5]([NH:12][C:11]1[CH:13]=[CH:14][CH:15]=[C:9]([F:8])[CH:10]=1)=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 97423-Fluoroaniline

Product 1

HCID 9594N-(3-Fluorophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of acetic anhydride (30.30 g, 0.297 mol) in glacial acetic acid (30 ml) is added to stirred 3-fluoroaniline (30.0 g, 0.27 mol). The resulting stirred mixture is heated under reflux for 20 minutes and poured into cold water (500 ml). the product is extracted into ether (×2) and the combined ethereal extracts are washed with water and dried (MgSO4). The solvent is removed in vacuo and the residue is recrystallized from aqueous acetic acid to yield colourless crystals with a yield of 28.90 g (70%).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 20 minutes
  3. extractionthe product is extracted into ether (×2)
  4. washthe combined ethereal extracts are washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent is removed in vacuo
  7. customthe residue is recrystallized from aqueous acetic acid
  8. customto yield colourless crystals with a yield of 28.90 g (70%)

Sources & evidence

ORD record
ord-c398c8443004483bacd83121f8be4daf
Source dataset
uspto-grants-1999_03
Patent number
US05888421

Reaction notes

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