Potassium Hydroxide → HCID 10957724, compound

Temperature

115 °C

In a mixture of ethanol (30 ml) and toluene (90 ml) was dissolved 1-amino-5-(2, 3-dichlorophenyl)cyclohexen-3-one (1.5 g), and to the solution were added 3-oxobutylaldehydedimethylacetal (2 g) and granulated potassium hydroxide (330 mg). The mixture was stirred at 115° C. (bath temperature), and to the mixture was added granulated potassium hydroxide (70 mg), 30 minutes later; 1 hour later; and 1.5 hours, respectively. The reaction solution was stirred at the same temperature for 1 hour, cooled and concentrated under reduced pressure, and to the residue were added ethyl acetate (50 ml) and water (20 ml). The mixture was shaken and separated ethyl acetate layer was washed with 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-(2,3-dichlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (1.05 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. temperaturecooled
5. concentrationconcentrated under reduced pressure
6. additionto the residue were added ethyl acetate (50 ml) and water (20 ml)
7. stirringThe mixture was shaken
8. customseparated ethyl acetate layer
9. washwas washed with brine
10. customUnder reduced pressure, ethyl acetate was evaporated
11. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)
12. washeluted with ethyl acetate/hexane

ORD record

ord-74fec995dba34707a9dfd71f13e60f74

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350749B1