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

HRID 1449567

Reaction equation

HRID 1449567 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-2,3dione (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-538c5ab905094dd6a93d5d5fdc38ecb0
Source dataset
uspto-grants-1997_02
Patent number
US05599814

Linked notes

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