반응 #466906

반응 방정식

3-acetylamino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole

KOH

→

title compound

수율 41.1%

3-Acetylamino-2-benzoyl-6-chloroindole

수율 41.1%

용매

ethanol water

반응 조건

후처리

1. 1
   온도the mixture was heated
2. 2
   온도at reflux temperature for 1 h
3. 3
   온도The mixture was cooled
4. 4
   농축concentrated
5. 5
   기타the residue partitioned between water (50 ml) and diethyl ether (100 ml)
6. 6
   추출The organic extract
7. 7
   세척was washed with water (100 ml)
8. 8
   기타After drying
9. 9
   기타(MgSO4) and removal of solvent
10. 10
    기타the crude product was recrystallized from dichloromethane/hexane

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

출처