Hydrogen Peroxide → 6-Chloro-5-fluoroisatoic acid anhydride

HRID 223332Notes

Reaction equation

HRID 223332 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:13])[C:5](=[O:12])[NH:6]2.S(=O)(=O)(O)[OH:15].OO>C(O)(=O)C>[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]2[NH:6][C:5](=[O:15])[O:12][C:4](=[O:13])[C:3]=12

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 149861234-chloro-5-fluoro-1H-indole-2,3-dione

Product 1

HCID 536626896-Chloro-5-fluoroisatoic acid anhydride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7.8 g (0.039 mol) of 4-chloro-5-fluoroisatin are suspended in 50 ml of 100 percent acetic acid, treated with 0.25 ml of concentrated sulphuric acid and then at 30° 4.4 ml (0.043 mol) of 30 percent hydrogen peroxide are added thereto. The mixture is subsequently heated to 70° for 2.5 hours, then cooled to 10° and filtered. The crude product is recrystallized from acetone/hexane, there being obtained 6-chloro-5-fluoroisatoic acid anhydride of melting point 275°-278° (decomposition).

Workup

  1. temperatureThe mixture is subsequently heated to 70° for 2.5 hours
  2. temperaturecooled to 10°
  3. filtrationfiltered
  4. customThe crude product is recrystallized from acetone/hexane, there

Sources & evidence

ORD record
ord-d65554ef1dce4c9cbe8ea8fcddad52ba
Source dataset
uspto-grants-1982_10
Patent number
US04353827

Reaction notes

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