Acetic Acid → 5-Ethyl-2H-3,1-benzoxazine-2,4(1H)-dione

HRID 965331Notes

Reaction equation

HRID 965331 reaction equation
C([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=O)C.S(=O)(=O)(O)O.OO.[C:21]([OH:24])(=[O:23])[CH3:22]>>[CH2:5]([C:4]1[CH:3]=[CH:11][CH:10]=[C:9]2[NH:8][C:7](=[O:12])[O:24][C:21](=[O:23])[C:22]=12)[CH3:6]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 5834875-ethyl-2,3-dihydro-1H-indole-2,3-dione

Product 1

HCID 120854095-Ethyl-2H-3,1-benzoxazine-2,4(1H)-dione

Procedure

5-Ethylisatin (70 g), acetic acid (200 ml) and concentrated sulfuric acid (0.8 ml) were charged in a 500 ml two-necked flask, followed by stirring at room temperature. Then, 50 ml of aqueous 30% hydrogen peroxide was added dropwise and, after stirring at 60° to 65° C. for additional one hour, the mixture was cooled. The deposited solid was filtered, washed with water and dried under vacuum to obtain 6-ethylisatoic anhydride. Crude yield: 35 g

Workup

  1. stirringafter stirring at 60° to 65° C. for additional one hour
  2. temperaturethe mixture was cooled
  3. filtrationThe deposited solid was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-a086a553a54d4f968e2073f11b96e634
Source dataset
uspto-grants-1998_06
Patent number
US05773613

Reaction notes

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