4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER synthesis
- Product Name:4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER
- CAS Number:26892-90-0
- Molecular formula:C12H11NO3
- Molecular Weight:217.22
54535-22-7
26892-90-0
General procedure for the synthesis of ethyl 4-hydroxyquinoline-3-carboxylate from diethyl 2-phenylaminomethylidene-malonate: In a 1L three-necked flask fitted with a mechanical stirrer, diethyl 2-phenylaminomethylidene-malonate (26.3 g, 0.100 mol), polyphosphoric acid (270 g), and phosphorochloride (750 g) were added. The reaction mixture was heated to 70 °C and stirred at this temperature for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and then filtered. The filtered residue was treated with aqueous sodium carbonate (Na2CO3), filtered again, washed with water and finally dried. Ethyl 4-hydroxyquinoline-3-carboxylate was obtained as a light brown solid (15.2 g, 70% yield).
Yield: 76%
Reaction Conditions:
in ethanol at 100 - 200; for 3 h;
Steps:
Ethyl 4-hydroxyquinoline-3-carboxylate
Aniline (1.02 mL, 0.011 mol) and diethyl ethoxymethylenemalonate (0.5-2 eq) were weighed into ethanol and heated at 100-200 ° C for three hours.Cool to room temperature, add phenyl ether, heat at 100-200 ° C for 30 min, cool to room temperature,After the reaction was completed, ice water was added, and ethyl acetate (100 mL × 2) was added, and the organic phase was combined, and the organic phase was washed with saturated brine.Dry over anhydrous sodium sulfate, filter,The organic phase was concentrated and the residue was purified by silica gel column chromatography1.6 g (76% yield);
References:
Ocean University of China;Shao Changlun;Li Debao;Jiao Yahan CN108623581, 2018, A Location in patent:Page/Page column 6
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