HCID 67377290, Verbindung → 2-Benzyl-6,7-dichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one
Reaktionsgleichung
[CH:1](=[C:8]1[CH2:20][CH2:19][C:18]2[C:17]3[C:12](=[CH:13][C:14]([Cl:22])=[C:15]([Cl:21])[CH:16]=3)[NH:11][C:10]=2[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[CH2:1]([CH:8]1[CH2:20][CH2:19][C:18]2[C:17]3[C:12](=[CH:13][C:14]([Cl:22])=[C:15]([Cl:21])[CH:16]=3)[NH:11][C:10]=2[C:9]1=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of 2-benzylidene-6,7-dichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.07 g, 0.20 mmol) in EtOAc (10 mL), 10% Pd/C (10 mg) was added under N2 atmosphere. The reaction mixture was stirred under H2 atmosphere at room temperature for 12 h. The reaction mixture was filtered through a Celite® pad. The Celite® pad was washed with EtOAc (2×20 mL) and the filtrate was concentrated in vacuo to provide the crude material which was purified by silica gel chromatography [EtOAc-hexane (1:9) as eluant] to furnish the title compound as a yellow solid (0.04 g, 57%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.79 (s, 1H), 7.73 (s, 1H), 7.54 (s, 1H), 7.34-7.31 (m, 2H), 7.25-7.22 (m, 3H), 3.48-3.45 (m, 1H), 3.02-2.97 (m, 1H), 2.86-2.81 (m, 2H), 2.80-2.66 (m, 1H), 2.25-2.21 (m, 1H), 1.95-1.92 (m, 1H).