2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2,3-Dichloro-8-methoxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one

HRID 2275238Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2275238
[O:1]1CCOCC1.[Cl:7][C:8]1[CH:9]=[C:10]2[C:18](=[CH:19][C:20]=1[Cl:21])[NH:17][C:16]1[C:15]([CH3:23])([CH3:22])[C:14]3[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:13]=3[CH2:12][C:11]2=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O>[Cl:7][C:8]1[CH:9]=[C:10]2[C:18](=[CH:19][C:20]=1[Cl:21])[NH:17][C:16]1[C:15]([CH3:22])([CH3:23])[C:14]3[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:13]=3[C:12](=[O:1])[C:11]2=1

Komponenten

5

Edukt 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 312751,4-DioxaneHCID 668349922,3-Dichloro-8-methoxy-6,6-dimethyl-6,11-dihydro-5H-benzo[b]carbazole

Produkt 1

HCID 668343702,3-Dichloro-8-methoxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-oneAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Under nitrogen atmosphere, to the 1,4-dioxane (1.7 mL)-water (0.1 mL) solution of 2,3-dichloro-8-methoxy-6,6-dimethyl-6,11-dihydro-5H-benzo[b]carbazole (Compound Y2, 61.0 mg, 0.176 mmol), DDQ (120 mg, 0.529 mmol) was added and the mixture was stirred at room temperature for 16 hr and 15 min. The reaction mixture was purified by flash column chromatography {Merck Kieselgel60, solution for elution:hexane/ethyl acetate (2:1)} to obtain the title compound (pale orange solid, 16.7 mg, 26%).

Aufarbeitung

  1. customThe reaction mixture was purified by flash column chromatography {Merck Kieselgel60, solution for elution

Quellen und Nachweise

ORD-Eintrag
ord-0ce7a85d67324774900ffe708398e469
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09126931B2

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