반응 #155313

반응 방정식

sodium thiosulfate

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

Potassium carbonate

iodine

→

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

수율 87.4%

용매

Ethyl acetate

DMF

반응 조건

후처리

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

실험 절차

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%).

출처