Water → 7-Fluoroisatin

HRID 497987

Reaction equation

HRID 497987 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:13])[CH:10]=NO.[OH2:14]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:8][C:9](=[O:13])[C:10]2=[O:14]

Participants

4

Reactant 2

HCID 962WaterHCID 6710880N-(2-fluorophenyl)-2-(hydroxyimino)acetamide

Product 1

HCID 5864187-FluoroisatinYield 46%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
70 °C

Procedure

A solution of N-(2-fluorophenyl)-2-(hydroxyimino)acetamide (35.0 g, 192 mmol) in sulfuric acid (150 mL) was heated and stirred at 70° C. for 45 minutes. The solution was allowed to cool to room temperature and poured into iced water, and organic matter was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting crystals were collected by filtration to give the title compound (14.6 g, 46% yield).

Workup

  1. temperatureto cool to room temperature
  2. extractionwas extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-e546cbf11300420e89834fc0987f4dee
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Linked notes

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