ethyl 4-chloro-8-methoxy-quinoline-3-carboxylate synthesis

5synthesis methods

Product Name:ethyl 4-chloro-8-methoxy-quinoline-3-carboxylate
CAS Number:27568-05-4
Molecular formula:C13H12ClNO3
Molecular Weight:265.69

27568-04-3 Synthesis

4-HYDROXY-8-METHOXY-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER

27568-04-3
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$6.00/250mg

ethyl 4-chloro-8-methoxy-quinoline-3-carboxylate

27568-05-4
54 suppliers
$56.00/250mg

Yield:27568-05-4 98 %

Reaction Conditions:

with trichlorophosphate in acetonitrile at 90;Inert atmosphere;

Steps:

88 Synthesis of ethyl 8-hydroxy-7-nitroquinoline-3-carboxylate (88)

At room temperature, phosphorus oxychloride (2.3mL, 24.3mmol) was added4-Hydroxy-8-methoxyquinoline-3-carboxylic acid ethyl ester (88a)(2.0 g, 8.1 mmol) in acetonitrile (20.0 mL). The reaction mixture was stirred at 90°C for 2.5 hours, cooled to room temperature, and concentrated under reduced pressure. The resulting residue was diluted with dichloromethane (30.0 mL), and triethylamine (4.91 g, 48.5 mmol) was added, stirred for 30 minutes, and filtered under reduced pressure. The filter cake was washed with dichloromethane (5.0 mL x 3), and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=3/1),4-Chloro-8-methoxyquinoline-3-carboxylic acid ethyl ester (88b) was obtained(2.1 g, 98% yield).

References:

WO2022/253152,2022,A1 Location in patent:Page/Page column 48; 105; 106

71082-34-3 Synthesis