m-Chloroperbenzoic acid → 6-Ethylisatoic anhydride

HRID 223327Notes

Reaction equation

HRID 223327 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5](=[O:13])[C:6](=[O:12])[NH:7]2)[CH3:2].ClC1C=CC=C(C(OO)=[O:22])C=1>C(O)(=O)C.C(OCC)(=O)C>[CH2:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[NH:7][C:6](=[O:22])[O:12][C:5](=[O:13])[C:4]=12)[CH3:2]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 138270824-Ethyl-1H-indole-2,3-dione

Product 1

HCID 120854096-Ethylisatoic anhydride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

20 g (0.114 mol) of 4-ethylisatin are suspended in 75 ml of 100 percent acetic acid, treated portionwise with 26 g (0.137 mol) of m-chloroperbenzoic acid, the temperature not rising above 50°, and then the mixture is stirred at this temperature for a further 15 minutes. The mixture is poured into ice-water and filtered. The crude product obtained is taken up in ethyl acetate and extracted cautiously with a mixture of 2 N sodium hydroxide and ice. The ethyl acetate phase is dried over magnesium sulphate and concentrated to give crude 6-ethylisatoic acid anhydride which melts at 202°-204° after recrystallization from ethyl acetate.

Workup

  1. customrising above 50°
  2. filtrationfiltered
  3. customThe crude product obtained
  4. extractionextracted cautiously with a mixture of 2 N sodium hydroxide and ice
  5. dry with materialThe ethyl acetate phase is dried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cf23b22930864cabac37ca1281952272
Source dataset
uspto-grants-1982_10
Patent number
US04353827

Reaction notes

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