Reacción #90102

Ecuación de reacción

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

Disolventes

THF

THF diethyl ether

water

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to room temperature
2. 2
   Lavadowashed with water, saturated aqueous solution of sodium hydrogen carbonate and saturated brine
3. 3
   Secadodried over magnesium sulfate
4. 4
   FiltraciónAfter filtration and concentration under reduced pressure
5. 5
   Otrothe residues obtained
6. 6
   workup.STIRRINGthe mixture was stirred at room temperature for 2 hr
7. 7
   Lavadowashed with 0.5 N aqueous solution of sodium hydroxide and saturated brine
8. 8
   SecadoAfter drying with sodium sulfate
9. 9
   Filtraciónthe mixture was filtered
10. 10
    Otrothe resulting residues obtained
11. 11
    Concentraciónafter concentration under reduced pressure
12. 12
    Lavadowere washed with the mixture liquid of hexane/diethyl ether (1:1)

Procedimiento

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).

Fuente