Reaktion #3243

Reaktionsgleichung

2-isopropylaminobenzaldehyde

diethyl malonate

sodium bicarbonate

→

ethyl 1-isopropyl-2(1H)-quinolone-3-carboxylate

Ausbeute 61.3%

Lösungsmittel

acetic anhydride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter evaporation of the solvent under reduced pressure, water
2. 2
   workup.ADDITIONwas added
3. 3
   Extraktionfollowed by extraction with ethyl acetate
4. 4
   WaschenThe organic layer was washed with water
5. 5
   Trocknena saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate
6. 6
   SonstigeThe solvent was evaporated under reduced pressure
7. 7
   Sonstigethe resulting oily substance was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Vorschrift

A solution of 7.5 g of 2-isopropylaminobenzaldehyde, 11.0 g of diethyl malonate and 11.6 g of sodium bicarbonate in 800 ml of acetic anhydride was stirred under heating at 100° C. for 15 hours. After evaporation of the solvent under reduced pressure, water was added, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting oily substance was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give 7.3 g of ethyl 1-isopropyl-2(1H)-quinolone-3-carboxylate.

Quelle