反応 #90059

反応方程式

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-hydrazino-benzonitrile

→

title compound

9-Bromo-8-methoxy-6,6-dimethyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

溶媒

TFA

反応条件

後処理

1. 1
   その他TFA was removed under reduced pressure
2. 2
   workup.ADDITIONthe residues were added with saturated aqueous solution of NaHCO3 (500 mL)
3. 3
   抽出followed by extraction with ethyl acetate
4. 4
   洗浄The organic layer was washed with saturated brine
5. 5
   乾燥dried over sodium sulfate
6. 6
   その他The drying agent was removed by filtration
7. 7
   その他the residues obtained
8. 8
   濃縮after concentration under reduced pressure
9. 9
   workup.ADDITIONwere added with ethyl acetate
10. 10
    workup.STIRRINGAfter stirring at room temperature
11. 11
    その他the precipitated solid was separated by filtration (Compound E2-2)
12. 12
    濃縮The filtrate was concentrated under reduced pressure

実験手順

6-Bromo-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound E1, 7.89 g, 27.85 mmol) and 3-hydrazino-benzonitrile (4.45 g, 1.2 eq.) were dissolved in TFA (250 mL), and stirred at 100° C. for 2 hr. TFA was removed under reduced pressure and the residues were added with saturated aqueous solution of NaHCO3 (500 mL), followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were added with ethyl acetate. After stirring at room temperature, the precipitated solid was separated by filtration (Compound E2-2). The filtrate was concentrated under reduced pressure to obtain the title compound as a mixture with E2-2 (yellowish white powder, 2.65 g).

出典