Potassium Hydroxide → 7-(2-Furyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one

Temperature

115 °C

In a mixture of ethanol (30 ml) and toluene (90 ml) was dissolved 1-amino-5-(2-furyl)cyclohexen-3-one (1.25 g), and to the solution were added 3-oxobutylaldehydedimethylacetal (2.36 g) and granulated potassium hydroxide (390 mg). The mixture was stirred at 115° C. (bath temperature), and to the mixture was added granulated potassium hydroxide (80 mg), 30 minutes later; 1 hour later; and 1.5 hours later; respectively. The reaction solution was stirred at the same temperature for 1 hour. The reaction solution was cooled, and concentrated under reduced pressure, and to the residue was added ethyl acetate (50 ml) and water (15 ml). The mixture was shaken and the separated upper layer was washed with saturated brine. Under reduced pressure, ethyl acetate was evaporated, and the residue was purified with silica gel column chromatography (EtOAc/hexane) and eluted with ethyl acetate/hexane to give 7-(2-furyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (1.0 g) as colorless crystals.

1. custom1 hour
2. custom1.5 hours
3. stirringThe reaction solution was stirred at the same temperature for 1 hour
4. temperatureThe reaction solution was cooled
5. concentrationconcentrated under reduced pressure
6. additionto the residue was added ethyl acetate (50 ml) and water (15 ml)
7. stirringThe mixture was shaken
8. washthe separated upper layer was washed with saturated brine
9. customUnder reduced pressure, ethyl acetate was evaporated
10. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)
11. washeluted with ethyl acetate/hexane

ORD record

ord-21d8176e2ab640c483653aa52a5198e7

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350749B1