N-Iodosuccinimide → 5-Iodoindolin-2-one

HRID 1369853Notes

Reaction equation

HRID 1369853 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 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 1.0 hour at 10° C. The suspended solid which had 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 sucked dry for 20 minutes in the funnel. The product was dried under vacuum to give 93.5 g (36%) of 5-iodo-2-oxindole containing about 5% 2-oxindole by proton NMR.

Workup

  1. additionAfter the addition
  2. stirringwas stirred for 1.0 hour at 10° C
  3. filtrationThe solid was collected by vacuum filtration
  4. washwashed with 100 mL of 50% acetic acid in water
  5. dry with materialwith 200 mL of water and sucked dry for 20 minutes in the funnel
  6. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-634414ddcbb148b4848858a9462a2f74
Source dataset
uspto-grants-2003_06
Patent number
US06579897B2

Reaction notes

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