Water → 5-Iodoindolin-2-one

HRID 1280742Notes

Reaction equation

HRID 1280742 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.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

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 321710Oxindole

Product 1

HCID 98380455-Iodoindolin-2-oneYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-indolinone (2.66 g, 20 mmol) in acetic acid (20 ml) was stirred at room temperature in the presence of N-iodosuccinimide (5.4 g, 24 mmol) for 2 hours. H2O (150 ml) was then added. The precipitate was filtered, washed with H2O, and dried. The resulting solid was refluxed in ethyl acetate (50 ml), cooled to 0° C., filtered, washed with ethylacetate and ether and dried to provide 5-iodo-1,3-dihydro-indol-2-one (3.62 g. 70%) as a beige solid, m.p. 190-192° C. and MS: m/e=259 (M+).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with H2O
  3. customdried
  4. temperatureThe resulting solid was refluxed in ethyl acetate (50 ml)
  5. filtrationfiltered
  6. washwashed with ethylacetate and ether
  7. customdried

Sources & evidence

ORD record
ord-a13e921ddcde46c3acab159af96600db
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

Loading…