Water → 5,7-Dimethyl-2H-3,1-benzoxazine-2,4(1H)-dione

HRID 3109

Reaction equation

HRID 3109 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]2[C:3]=1[C:4](=[O:13])[C:5](=[O:12])[NH:6]2.[OH2:14]>C(O)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[CH3:1][C:2]1[C:3]2[C:4](=[O:13])[O:12][C:5](=[O:14])[NH:6][C:7]=2[CH:8]=[C:9]([CH3:11])[CH:10]=1

Participants

5

Reactant 2

HCID 962WaterHCID 23861614,6-dimethyl-1H-indole-2,3-dione

Product 1

HCID 189298545,7-Dimethyl-2H-3,1-benzoxazine-2,4(1H)-dioneYield 31%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred warm (60° C.) solution of 4,6-dimethyl-1H-indole-2,3-dione (2.0 g, 11.4 mM) in acetic acid (20 mL) was added in small portions chromium trioxide (6.6 g, 66 mM) while maintaining the temperature of the reaction mixture at 65°-70° C. The reaction mixture was then heated at 80° C. for one hour, cooled, poured into water (150 mL) and filtered to obtain the the title compound (0.67 g, 31%) as a light yellow solid; MS(CI): 192 (M+H).

Workup

  1. temperaturewhile maintaining the temperature of the reaction mixture at 65°-70° C
  2. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-ed246c15161e44ccb5ed8c113f70f2e4
Source dataset
uspto-grants-1998_03
Patent number
US05733910

Linked notes

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