p-Chlorophenacyl bromide → 1-(4-chlorophenyl)-8,9-dihydro-7H-pyrrolo[3,2,1-ij]quinolin-7-one

5,6,7,8-Tetrahydroquinolin-5-one (35 g) was dissolved in 80 ml of toluene. To this solution was added 4-chlorophenacyl bromide (55.6 g) gradually and refluxed for 18 hours. The reaction mixture was cooled to room temperature, and depositing crystals were collected by filtration (78 g). These solids were dissolved in 700 ml of N,N-dimethylformamide. To this solution was added, molecular sieves 3A (30 g) and triethylamine (34 ml), then the reaction mixture was heated at 100° C. for 1 hour. The reaction mixture became dark brown. The dark brown solution that obtained after removing insoluble matter by filtration was concentrated under reduced pressure. To the residue was added 300 ml of water, and extracted with 200 ml of methylene chloride three times. This methylene chloride solution was washed with 100 ml of brine and dried over anhydrous sodium sulfate. The dark brown solution that obtained after removing drying agent by filtration was concentrated under reduced pressure, the resultant dark brown residue was purified by alumina column chromatography. The title compound was obtained as dark red crystals (29 g).

1. temperaturerefluxed for 18 hours
2. filtrationdepositing crystals were collected by filtration (78 g)
3. dissolutionThese solids were dissolved in 700 ml of N,N-dimethylformamide
4. additionTo this solution was added
5. temperaturemolecular sieves 3A (30 g) and triethylamine (34 ml), then the reaction mixture was heated at 100° C. for 1 hour
6. customThe dark brown solution that obtained
7. customafter removing insoluble matter
8. filtrationby filtration
9. concentrationwas concentrated under reduced pressure
10. additionTo the residue was added 300 ml of water
11. extractionextracted with 200 ml of methylene chloride three times
12. washThis methylene chloride solution was washed with 100 ml of brine
13. dry with materialdried over anhydrous sodium sulfate
14. customThe dark brown solution that obtained
15. customafter removing
16. customdrying agent
17. filtrationby filtration
18. concentrationwas concentrated under reduced pressure
19. customthe resultant dark brown residue was purified by alumina column chromatography

ORD 기록

ord-1faaa3ca9f9647c4b6fd13a47020a9dc

출처 데이터셋

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05643920