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

HRID 236376

반응식

HRID 236376 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-f9a0555eb1754bb7895036c67bbca9ce
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04644005

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