N-Iodosuccinimide → 5-Iodoindolin-2-one

HRID 1860750Notes

Reaction equation

HRID 1860750 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[I:11]N1C(=O)CCC1=O>C(O)(=O)C>[I:11][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][C:2](=[O:10])[CH2:3]2

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 321710Oxindole

Product 1

HCID 98380455-Iodoindolin-2-oneYield 58%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

2-Oxindole (82.9 g) was suspended in 630 ml of acetic acid in a reaction vessel equipped with mechanical stirring and the mixture cooled to 10° C. in an ice water bath. Solid N-iodosuccinimide (175 g) was added in portions over 10 minutes. After the addition was complete the mixture was stirred for 1 hour at 10° C. The suspended solid which was always present became very thick at this time. The solid was collected by vacuum filtration, washed with 100 ml of 50% acetic acid in water and then with 200 ml of water and subjected to vacuum filtration for 20 minutes to partially air dry it. The product was then dried under vacuum to give 93.5 g (36%) of 5-iodo-2-oxindole containing about 5% 2-oxindole by proton NMR.

Workup

  1. customequipped
  2. additionAfter the addition
  3. stirringwas stirred for 1 hour at 10° C
  4. filtrationThe solid was collected by vacuum filtration
  5. washwashed with 100 ml of 50% acetic acid in water
  6. filtrationwith 200 ml of water and subjected to vacuum filtration for 20 minutes
  7. customto partially air dry it
  8. customThe product was then dried under vacuum

Sources & evidence

ORD record
ord-4354004d6ae94c43bd0e37aaf5b1beab
Source dataset
uspto-grants-2003_03
Patent number
US06531502B1

Reaction notes

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