Tetrahydrofuran → 4-Methyl-7-(2-thienyl)-5,6,7,8-tetrahydroquinolin-5-one

To a mixture of 5-(2-thienyl)cyclohexane-1,3-dione (1.5 g), 1-amino-2-butyne hydrochloride (0.82 g), molecular sieves 4A (3 g) and tetrahydrofuran (30 ml) was added triethylamine (0.78 g). The mixture was stirred at room temperature for 1 hour, refluxed for refluxed for 12 hours and cooled, and insoluble materials were filtered off. Under reduced pressure, the solvent was evaporated, and to the residue was added diphenylether (80 ml), and the mixture was stirred at 250° C. for 6 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The solution was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/hexane) to give colorless crystals of 4-methyl-7-(2-thienyl)-5,6,7,8-tetrahydroquinolin-5-one (0.67 g).

1. temperaturerefluxed
2. temperaturefor refluxed for 12 hours
3. temperaturecooled
4. filtrationinsoluble materials were filtered off
5. customUnder reduced pressure, the solvent was evaporated
6. additionto the residue was added diphenylether (80 ml)
7. stirringthe mixture was stirred at 250° C. for 6 hours
8. customUnder reduced pressure, the solvent was evaporated
9. dissolutionthe residue was dissolved in ethyl acetate
10. washThe solution was washed with water and saturated brine
11. dry with materialdried with magnesium sulfate
12. concentrationconcentrated under reduced pressure
13. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)

ORD record

ord-3ee3a70c3ff240c28983933295f79340

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350749B1