Water → 7-Iodo-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 3119

Reaction equation

HRID 3119 reaction equation
[I:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:12])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[OH2:13]>C(O)(=O)C.C(OC(=O)C)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:12])[O:11][C:7](=[O:13])[NH:8][C:9]=2[CH:10]=1

Participants

6

Reactant 2

HCID 962WaterHCID 143872746-iodo-2,3-dihydro-1H-indole-2,3-dione

Product 1

HCID 189299207-Iodo-1H-benzo[d][1,3]oxazine-2,4-dioneYield 81.8%

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred warm (80° C.) solution of 6-iodo-1H-indole-2,3-dione (3.0 g, 11 mM) in acetic acid (10 mL) and acetic anhydride (10 mL) was added in small portions chromium trioxide (1.83 g, 18.3 mM) while maintaining the temperature of the reaction mixture at 80°-90° C. The reaction mixture was then heated at 80° C. for 10 min, cooled and poured into water. The resulting mixture was filtered and the collected solids dried to provide the title compound as a yellow solid (2.6 g, 81.8%); MS(CI): 290 (M+H).

Workup

  1. temperaturewhile maintaining the temperature of the reaction mixture at 80°-90° C
  2. temperaturecooled
  3. filtrationThe resulting mixture was filtered
  4. customthe collected solids dried

Sources & evidence

ORD record
ord-57ce19bea6534a878ad8a04143464a6c
Source dataset
uspto-grants-1998_03
Patent number
US05733910

Linked notes

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