Diethyl Malonate → Ethyl 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylate

반응식

[CH:1]([NH:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=O)([CH3:3])[CH3:2].[C:13](OCC)(=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])O.[Na+]>C(OC(=O)C)(=O)C>[CH:1]([N:4]1[C:5]2[C:6](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:13]1=[O:20])([CH3:3])[CH3:2]

참가 물질

실험 절차

A solution of 7.5 g of 2-isopropylaminobenzaldehyde, 11.0 g of diethyl malonate and 11.6 g of sodium hydrogen carbonate in 80 ml of acetic anhydride was stirred at 100° C. for 15 hours. After the solvent was removed by distillation in vacuo, water was added to the residue. The mixture was then extracted with ethyl acetate. After the organic layer was washed with water and then with saturated sodium bicarbonate aqueous solution, the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off in vacuum. The resulting oily substance was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to obtain 7.3 g of ethyl 1-isopropyl-2(1H)-quinolone-3-carboxylate.