Acetic Acid → 5,6-Dichloroisatoic anhydride

HRID 1154465Notes

Reaction equation

HRID 1154465 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:13])[C:5](=[O:12])[NH:6]2.C(O)(=[O:16])C>C(OC(=O)C)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[Cl:11][C:10]1[C:2]([Cl:1])=[C:3]2[C:4]([O:12][C:5](=[O:16])[NH:6][C:7]2=[CH:8][CH:9]=1)=[O:13]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 51399804,5-Dichloro-1H-indole-2,3-dione

Product 1

HCID 541214315,6-Dichloroisatoic anhydride

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

49 g (0.226 mol) of 4,5-dichloroisatin are suspended in 200 ml of acetic acid and 200 ml of acetic anhydride, treated over a period of 50 minutes at a temperature between 80° and 90° with 37.65 g (0.376 mol) of chromium trioxide and the mixture is subsequently cooled to 5°. The precipitated material is filtered off under suction, washed with water and dried. There is obtained 5,6-dichloroisatoic acid anhydride of melting point 280°-283°.

Workup

  1. temperaturethe mixture is subsequently cooled to 5°
  2. filtrationThe precipitated material is filtered off under suction
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-791f6d53bf52469a81fc7bf34ec27dca
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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