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ChemicalBook CAS DataBase List 6-Quinolinecarboxylic acid, 4-(4-amino-3-chlorophenoxy)-7-methoxy-, methyl ester
417723-07-0

6-Quinolinecarboxylic acid, 4-(4-amino-3-chlorophenoxy)-7-methoxy-, methyl ester synthesis

5synthesis methods
205448-66-4 Synthesis
Methyl 4-chloro-7-Methoxyquinoline-6-carboxylate

205448-66-4
219 suppliers
$9.00/250mg

17609-80-2 Synthesis
4-Amino-3-chlorophenol

17609-80-2
316 suppliers
$39.00/5g

6-Quinolinecarboxylic acid, 4-(4-amino-3-chlorophenoxy)-7-methoxy-, methyl ester

417723-07-0
19 suppliers
inquiry

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Yield:-

Reaction Conditions:

in dimethyl sulfoxide;ethyl acetate;

Steps:

P.395.1 Methyl 4-(4-amino-3-chlorophenoxy)-7-methoxy-6-quinolinecarboxylate

Production Example 395-1 Methyl 4-(4-amino-3-chlorophenoxy)-7-methoxy-6-quinolinecarboxylate After dissolving 4-amino-3-chlorophenol (3.17 g, 22.05 mmol) in dimethylsulfoxide (50 ml), sodium hydride (882 mg, 22.05 mmol) was gradually added at room temperature and the mixture was stirred for 30 minutes. The 4-chloro-7-methoxy-6-methoxycarbonylquinoline (3.70 g, 14.7 mmol) described in WO0050405 was added, and the mixture was heated at 100° C. for 3 hours. After standing to cool to room temperature, the reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off, silica gel column chromatography (eluent-ethyl acetate) was performed, the fraction containing the target substance was concentrated, suspended in ethyl acetate and diluted with hexane, and the crystals were filtered out and blow-dried to obtain the title compound (3.092 g, 8.62 mmol, 57.4%) as light brown crystals. 1H-NMR Spectrum (CDCl3) δ (ppm): 3.98 (3H, s), 4.06 (3H, s), 4.12 (2H, s), 6.44 (1H, d, J=5.2 Hz), 6.86 (1H, d, J=8.8 Hz), 6.95 (1H, dd, J=2.8, 8.8 Hz), 7.16 (1H, d, J=2.8 Hz), 7.49 (1H, s), 8.64 (1H, d, J=5.2 Hz), 8.80 (1H, s).

References:

US2004/53908,2004,A1

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