Chlorosuccinimide → 7-Acetyl-1,3-dihydro-2H-indol-2-one

HRID 236376

Reaction equation

HRID 236376 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2)(=[O:3])[CH3:2].ClN1C(=[O:19])CCC1=O>C(Cl)Cl>[C:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10](=[O:19])[CH2:9]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 137705341-(1H-indol-7-yl)ethanone

Product 1

HCID 137705297-Acetyl-1,3-dihydro-2H-indol-2-oneYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 12.57 g. (79 mmoles) of 7-acetylindole in 187 ml. of methylene chloride was added 11.07 g. (82.9 mmoles) of N-chlorosuccinimide and the reaction allowed to stir at room temperature for 2 hours. The solvent was removed in vacuo and the residue treated with 155 ml. of acetic acid and heated to 80° C. Phosphoric acid (80 ml.) was added and the reaction mixture heated to reflux for 9 hours. The mixture was cooled, the acetic acid removed under vacuum and the residue poured into 500 ml. of ice and water. The product was extracted with methylene chloride, 11.91 g. (65% yield), 174°-175° C.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue treated with 155 ml
  3. temperatureof acetic acid and heated to 80° C
  4. additionPhosphoric acid (80 ml.) was added
  5. temperaturethe reaction mixture heated
  6. temperatureto reflux for 9 hours
  7. temperatureThe mixture was cooled
  8. customthe acetic acid removed under vacuum
  9. additionthe residue poured into 500 ml
  10. extractionThe product was extracted with methylene chloride, 11.91 g
  11. custom(65% yield), 174°-175° C.

Sources & evidence

ORD record
ord-f9a0555eb1754bb7895036c67bbca9ce
Source dataset
uspto-grants-1987_02
Patent number
US04644005

Linked notes

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