Chlorosuccinimide → 1-(Thiophen-3-yl)-1,3-dihydro-2H-indol-2-one

HRID 751343Notes

Reaction equation

HRID 751343 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7]2)=[CH:2]1.ClN1C(=[O:21])CCC1=O>ClCCl>[S:1]1[CH:5]=[CH:4][C:3]([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][C:7]2=[O:21])=[CH:2]1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 14819382HCID 14819382, compound

Product 1

HCID 148193781-(Thiophen-3-yl)-1,3-dihydro-2H-indol-2-oneYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of the above 1-(thien-3-yl)-1H-indole (6.10 g, 30.6 mmol), N-chlorosuccinimide (4.30 g, 32.2 mmol) and dichloromethane (230 mL) is stirred for 2 hr at room temperature. The solvent is then removed, the residue is dissolved in acetic acid (127 mL) and heated to 70° C. Then 85% phosphoric acid is added and the reaction mixture is heated at gentle reflux for 24 hr. After cooling to room temperature, the reaction is concentrated to about its volume, poured onto ice and water and extracted with ethyl acetate. The combined extract is washed with water, with brine, dried, filtered and concentrated. The black residue is purified by chromatography eluting with dichloromethane-0 to 5% methanol. Product containing fractions are combined and concentrated to afford 1-(thien-3-yl)-1H-indol-2-one (4.12 g, 63% yield) as a brown solid.

Workup

  1. customThe solvent is then removed
  2. dissolutionthe residue is dissolved in acetic acid (127 mL)
  3. additionThen 85% phosphoric acid is added
  4. temperaturethe reaction mixture is heated
  5. temperatureat gentle reflux for 24 hr
  6. temperatureAfter cooling to room temperature
  7. concentrationthe reaction is concentrated to about its volume
  8. additionpoured onto ice and water
  9. extractionextracted with ethyl acetate
  10. extractionThe combined extract
  11. washis washed with water, with brine
  12. customdried
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe black residue is purified by chromatography
  16. washeluting with dichloromethane-0 to 5% methanol
  17. additionProduct containing fractions
  18. concentrationconcentrated

Sources & evidence

ORD record
ord-7e28342d2cf741dea8787cd33a91c81f
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

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