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

HRID 1154493Notes

Reaction equation

HRID 1154493 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-fluoro-isatin are suspended in 50 ml of 100 percent acetic acid, treated with 0.25 ml of concentrated sulphuric acid and then 4.4 ml (0.043 mol) of 30 percent hydrogen peroxide are added dropwise 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-fluoro-isatoic 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-237ba3d8d381429797a0ca0eda6b6169
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

Loading…