Potassium Hydroxide → 3-Acetylamino-2-benzoyl-6-chloroindole

HRID 379724노트

반응식

HRID 379724 반응식
[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[N:7](C(OCC)=O)[C:6]=1[C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:3])[CH3:2].[OH-].[K+]>C(O)C.O>[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 183680413-Acetylamino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole

생성물 1

HCID 98397823-Acetylamino-2-benzoyl-6-chloroindole수율 41.1%

시약·촉매·용매 1

HCID 19096565Water ethanol용매

실험 절차

To a solution of 3-acetylamino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole (556 mg, 1.4 mmol) in ethanol/water (3:1, 20 ml) was added KOH (85% pellets, 480 mg, 7.2 mmol) and the mixture was heated at reflux temperature for 1 h. The mixture was cooled and concentrated, and the residue partitioned between water (50 ml) and diethyl ether (100 ml). The organic extract was washed with water (100 ml) and then brine (100 ml). After drying (MgSO4) and removal of solvent, the crude product was recrystallized from dichloromethane/hexane to afford 180 mg (41%) of the title compound as a yellow powder. m.p.: 212-213° C. 1H-NMR (CDCl3) δ: 9.90 (1H, br s), 8.29-8.15 (2H, m), 7.84-7.75 (2H, m), 7.70-7.52 (3H, m), 7.32-7.27 (1H, m), 7.12 (1H, dd, J=1.83, 9.16 Hz), 2.26 (3H, s). IR (KBr) ν: 3400, 1680, 1640, 1520, 1320 cm−1

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 1 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. customthe residue partitioned between water (50 ml) and diethyl ether (100 ml)
  6. extractionThe organic extract
  7. washwas washed with water (100 ml)
  8. customAfter drying
  9. custom(MgSO4) and removal of solvent
  10. customthe crude product was recrystallized from dichloromethane/hexane

출처 및 근거

ORD 기록
ord-bf541cafd8784442ae8514558254ffe3
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300363B1

반응 노트

불러오는 중…