تفاعل #155313

معادلة التفاعل

sodium thiosulfate

5-Propoxy-4H-benzo[f]quinolin-1-one

Potassium carbonate

iodine

→

2-iodo-5-propoxy-4H-benzo[f]quinolin-1-one

المردود 87.4%

المذيبات

Ethyl acetate

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGby stirring for 5 minutes
2. 2
   workup.STIRRINGstirred
3. 3
   ترشيحSubsequently, insoluble matter was collected by filtration
4. 4
   أخرىthe filtrate was then separated
5. 5
   غسيلThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution
6. 6
   تركيزconcentrated to dryness under reduced pressure
7. 7
   workup.ADDITIONThe residue was added to the collected insoluble matter
8. 8
   أخرىfollowed by purification
9. 9
   تركيزThe purified product was concentrated to dryness under reduced pressure

الإجراء التجريبي

5-Propoxy-4H-benzo[f]quinolin-1-one (2.66 g, 10.5 mmol) was suspended in DMF (20 ml). Potassium carbonate (1.63 g, 11.8 mmol) and iodine (2.95 g, 11.6 mmol) were added to the suspension, followed by stirring at room temperature for 3 hours. The reaction mixture was poured into an aqueous sodium thiosulfate solution (9.14 g, 100 ml), followed by stirring for 5 minutes. Ethyl acetate was added to the reaction mixture and stirred. Subsequently, insoluble matter was collected by filtration, and the filtrate was then separated. The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution, and then concentrated to dryness under reduced pressure. The residue was added to the collected insoluble matter, followed by purification using silica gel column chromatography (dichloromethane:methanol=50:1→20:1). The purified product was concentrated to dryness under reduced pressure, giving a pale brown powder of 2-iodo-5-propoxy-4H-benzo[f]quinolin-1-one (3.48 g, yield: 87%).

المصدر