تفاعل #90080

معادلة التفاعل

DDQ

6-Methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

3-bromophenylhydrazine hydrochloric acid salt

ethyl acetate

→

title compound

المردود 46.0%

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

المردود 46.0%

المذيبات

water

acetic acid

MTBE

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling
2. 2
   غسيلwashed with water, saturated aqueous solution of sodium hydrogen carbonate, and saturated brine
3. 3
   تجفيفdried over magnesium sulfate
4. 4
   ترشيحAfter the filtration, it
5. 5
   تركيزwas concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONThe resulting residues were dissolved in THF (30 mL)
7. 7
   workup.STIRRINGstirred at room temperature overnight
8. 8
   غسيلwashed with 0.5 N aqueous solution of sodium hydroxide and saturated brine
9. 9
   تجفيفdried over magnesium sulfate
10. 10
    ترشيحAfter filtration
11. 11
    تركيزthe concentration under reduced pressure
12. 12
    غسيلthe resulting residues were washed with MTBE

الإجراء التجريبي

6-Methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound J2, 2.15 g, 10.5 mmol) and 3-bromophenylhydrazine hydrochloric acid salt (3.11 g, 1.3 eq.) were dissolved in acetic acid (12 mL), and stirred at 100° C. for 2.5 hr under nitrogen atmosphere. After cooling, 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 the filtration, it was concentrated under reduced pressure. The resulting residues were dissolved in THF (30 mL) and water (3 mL), added with DDQ (5.96 g, 2.5 eq.) at 0° C., and then stirred at room temperature overnight. The reaction solution was added with MTBE, washed with 0.5 N aqueous solution of sodium hydroxide and saturated brine, and dried over magnesium sulfate. After filtration and the concentration under reduced pressure, the resulting residues were washed with MTBE to obtain the title compound (brown solid, 1.80 g, 46%).

المصدر