ChemicalBook CAS DataBase List methyl 4-chloroquinoline-7-carboxylate

methyl 4-chloroquinoline-7-carboxylate synthesis

6synthesis methods

Product Name:methyl 4-chloroquinoline-7-carboxylate
CAS Number:178984-69-5
Molecular formula:C11H8ClNO2
Molecular Weight:221.64

4-OXO-1,4-DIHYDRO-QUINOLINE-7-CARBOXYLIC ACID METHYL ESTER

863785-96-0

178984-69-5

General procedure for the synthesis of methyl 4-chloroquinoline-7-carboxylate from methyl 4-oxo-1,4-dihydroquinoline-7-carboxylate: the residue (0.59 g) was dissolved in N,N-dimethylformamide (20 ml), triethylamine (4 ml) and 10% palladium/carbon (0.59 g) were added. The reaction mixture was stirred overnight under hydrogen atmosphere and at room temperature. After completion of the reaction, the mixture was filtered and the filter cake was washed with chloroform. The solvent was removed by distillation under reduced pressure and the residue was washed with methanol to afford methyl 4-oxo-1,4-dihydroquinoline-7-carboxylate (187 mg, 28% yield). The resulting methyl 4-oxo-1,4-dihydroquinoline-7-carboxylate (650 mg) was suspended in diisopropylethylamine (7 ml), phosphorus trichloride (1.5 ml) was added, and the reaction was stirred at 120 °C for 30 min. After completion of the reaction, water was added to the reaction mixture under ice bath cooling. The aqueous layer was neutralized with aqueous sodium bicarbonate and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure and the residue was purified by column chromatography in acetone-chloroform system to afford methyl 4-chloroquinoline-7-carboxylate (609 mg, 86% yield).

863785-96-0
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$155.00/100mg

178984-69-5
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$65.00/100mg

Yield: 86%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine;trichlorophosphate at 120; for 0.5 h;

Steps:

113
A part of the residue (0.59 g) was dissolved in N,N-dimethylformamide (20 ml). Triethylamine (4 ml) and 10% palladium/carbon (0.59 g) were added to the solution, and the mixture was stirred under a hydrogen gas atmosphere at room temperature overnight. The reaction mixture was filtered and was then washed with chloroform. The solvent was removed by distillation under the reduced pressure, and the residue was washed with methanol to give methyl 4-oxo-1,4-dihydro-quinoline-7-carboxylate (187 mg, yield 28%) (3 steps). Methyl 4-oxo-1,4-dihydro-quinoline-7-carboxylate (650 mg) was suspended in diisopropylethylamine (7 ml), phosphorus oxychloride (1.5 ml) was added to the suspension, and the mixture was stirred at 120°C for 30 min. Water was added to the reaction mixture under ice cooling. The aqueous layer was neutralized with an aqueous sodium hydrogencarbonate solution, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-chloroform system to give methyl 4-chloro-quinoline-7-carboxylate (609 mg, yield 86%).

References:

KIRIN BEER KABUSHIKI KAISHA EP1724268, 2006, A1 Location in patent:Page/Page column 76

49713-58-8 Synthesis