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

温度

115 °C

In a mixture of ethanol (30 ml) and toluene (90 ml) was dissolved 1-amino-5-(5-methyl-2-thienyl)cyclohexen-3-one (1.66 g). To the solution were added 3-oxobutylaldehydedimethylacetal (2.6 g) and granulated potassium hydroxide (430 mg), and the mixture was stirred at 115° C. (bath temperature). To the mixture were added granulated potassium hydroxide (80 mg), 30 minutes later; 1 hour later; 1.5 hours later; respectively. The reaction solution was stirred at the same temperature for 1 hour and cooled. Under reduced pressure, the solvent was evaporated, and to the residue were added ethyl acetate (50 ml) and water (10 ml). The mixture was shaken, and the separated upper layer was washed with saturated brine and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (EtOAc/hexane) and eluted with ethyl acetate/hexane to give 4-methyl-7-(5-methyl-2-thienyl)-5,6,7,8-tetrahydroquinolin-5-one (1.78 g) as pale yellow oil.

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

ORDレコード

ord-6d5ec2d12f3a435a8b9355c98f17c2d2

出典データセット

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06350749B1