N-Iodosuccinimide → 7-Iodo-4-(trifluoromethyl)-1H-indole-2,3-dione

HRID 1369082Notes

Reaction equation

HRID 1369082 reaction equation
[F:1][C:2]([F:15])([F:14])[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.[I:16]N1C(=O)CCC1=O>OS(O)(=O)=O>[I:16][C:9]1[CH:10]=[CH:11][C:3]([C:2]([F:1])([F:14])[F:15])=[C:4]2[C:8]=1[NH:7][C:6](=[O:12])[C:5]2=[O:13]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 126294174-(Trifluoromethyl)-1H-indole-2,3-dione

Product 1

HCID 185185657-Iodo-4-(trifluoromethyl)-1H-indole-2,3-dioneYield 42%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-trifluoromethylisatin (450 mg, 2.09 mmol) and N-iodosuccinimide (800 mg, 3.72 mmol) in conc. H2SO4 (5 mL) was stirred for 6 h at 40° C. and poured into crushed ice. The mixture was extracted with ethyl acetate and the extracts were washed with aqueous Na2SO3, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography with 3:1 hexane/ethyl acetate to give the title compound (296 mg, 42%).

Workup

  1. additionpoured
  2. custominto crushed ice
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extracts were washed with aqueous Na2SO3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography with 3:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-200d528cbf4d4f4faa879521d7acd9e1
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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