Reaktion #90102

Reaktionsgleichung

ethyl acetate

6-Bromo-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

Compound E1

6-Bromo-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

3-chlorophenylhydrazine hydrochloric acid salt

DDQ

→

title compound

9-Bromo-3-chloro-8-methoxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one

Lösungsmittel

THF

THF diethyl ether

water

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   Waschenwashed with water, saturated aqueous solution of sodium hydrogen carbonate and saturated brine
3. 3
   Trocknendried over magnesium sulfate
4. 4
   FiltrationAfter filtration and concentration under reduced pressure
5. 5
   Sonstigethe residues obtained
6. 6
   workup.STIRRINGthe mixture was stirred at room temperature for 2 hr
7. 7
   Waschenwashed with 0.5 N aqueous solution of sodium hydroxide and saturated brine
8. 8
   TrocknenAfter drying with sodium sulfate
9. 9
   Filtrationthe mixture was filtered
10. 10
    Sonstigethe resulting residues obtained
11. 11
    Einengenafter concentration under reduced pressure
12. 12
    Waschenwere washed with the mixture liquid of hexane/diethyl ether (1:1)

Vorschrift

6-Bromo-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound E1, 0.2 g, 0.71 mmol) and 3-chlorophenylhydrazine hydrochloric acid salt (0.17 g, 1.3 eq.) were dissolved in acetic acid (0.5 mL). Under nitrogen atmosphere, the reaction solution was stirred at 90° C. for 8 hr. After cooling to room temperature, the reaction solution was added with ethyl acetate, washed with water, saturated aqueous solution of sodium hydrogen carbonate and saturated brine and dried over magnesium sulfate. After filtration and concentration under reduced pressure, the residues obtained therefrom were dissolved in THF (3 mL) comprising 10% water, added with DDQ (227 mg, 3 eq.) at room temperature, and the mixture was stirred at room temperature for 2 hr. The reaction solution was added with the mixture liquid of THF/diethyl ether (1:1) and washed with 0.5 N aqueous solution of sodium hydroxide and saturated brine. After drying with sodium sulfate, the mixture was filtered and the resulting residues obtained after concentration under reduced pressure were washed with the mixture liquid of hexane/diethyl ether (1:1) to obtain the title compound (brown powder, 86 mg).

Quelle