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ChemicalBook CAS DataBase List 4-Quinolinecarboxylicacid,3-hydroxy-,methylester(9CI)
73776-18-8

4-Quinolinecarboxylicacid,3-hydroxy-,methylester(9CI) synthesis

2synthesis methods
-

Yield:73776-18-8 48%

Reaction Conditions:

with dmap;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane; for 40 h;

Steps:

70.1

To a suspension of 3-hydroxyquinoline-4-carboxylic acid (4.977 g, 26.3 mmol) in CH2C12 (263 mL) was added MeOH (53.4 mL, 1.32 mol), 1-(3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride (EDCI, 5.55 g, 28.9 mmol), and 4-dimethylamino-pyridine (321 mg, 2.63 mmol). After 40 h, the mixture was concentrated and the residue was taken up in EtOAc and washed with H20. The aqueous layer was extracted with EtOAc. The combined extracts were washed with brine, dried over Na2504, filtered, and concentrated. The residue was purified by flash chromatography to provide methyl 3-hydroxyquinoline-4-carboxylate (2.56 g, 48 % yield) as an off-white solid. LC-MS mz 204 (MH).

References:

WO2015/71393,2015,A1 Location in patent:Page/Page column 162

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