反応 #155313

反応方程式

sodium thiosulfate

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

Potassium carbonate

iodine

→

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

収率 87.4%

溶媒

Ethyl acetate

DMF

反応条件

後処理

1. 1
   workup.STIRRINGby stirring for 5 minutes
2. 2
   workup.STIRRINGstirred
3. 3
   ろ過Subsequently, insoluble matter was collected by filtration
4. 4
   その他the filtrate was then separated
5. 5
   洗浄The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution
6. 6
   濃縮concentrated to dryness under reduced pressure
7. 7
   workup.ADDITIONThe residue was added to the collected insoluble matter
8. 8
   その他followed by purification
9. 9
   濃縮The purified product was concentrated to dryness under reduced pressure

実験手順

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%).

出典