O-Xylene → 5(6H)-Quinolinone, 7,8-dihydro-

Temperature

160 °C

In a nitrogen atmosphere, 24 mL of malonaldehyde tetraethyl acetal and 7.71 g of ammonium acetate were added in that order to xylene (80 mL) solution of 11.2 g of 1,3-cyclohexadione, and a reflux condenser tube fitted with a Dean-Stark water separator was attached to the reactor, and this was stirred at 160° C. for 18 hours. The reaction liquid was cooled to room temperature, the solvent was evaporated off under reduced pressure, the residue was extracted with chloroform, and the chloroform layer was washed with saturated saline water and dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was separated and purified through silica gel column chromatography (chloroform/methanol=97/3) to obtain 2.21 g of the entitled compound.

1. customThe reaction liquid
2. temperaturewas cooled to room temperature
3. customthe solvent was evaporated off under reduced pressure
4. extractionthe residue was extracted with chloroform
5. washthe chloroform layer was washed with saturated saline water
6. dry with materialdried with anhydrous sodium sulfate
7. customThe solvent was evaporated off under reduced pressure
8. customthe residue was separated
9. custompurified through silica gel column chromatography (chloroform/methanol=97/3)

ORD record

ord-bc30431459ad409882f2d8150a04874f

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07855294B2