Methyl quinoline-5-carboxylate

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Methyl quinoline-5-carboxylate manufacturers

Methyl quinoline-5-carboxylate Basic information
Product Name:Methyl quinoline-5-carboxylate
Synonyms:Methyl quinoline-5-carboxylate;5-Quinoline-carboxylic acid methyl ester;Methyl 5-quinolinecarboxylate;Quinoline-5-carboxylic acid Methyl ester;Methyl quinoline-5-carboxylate ISO 9001:2015 REACH
CAS:16675-62-0
MF:C11H9NO2
MW:187.19
EINECS:
Product Categories:Esters;Quinolines, Isoquinolines & Quinoxalines;Quinolines, Isoquinolines & Quinoxalines
Mol File:16675-62-0.mol
Methyl quinoline-5-carboxylate Structure
Methyl quinoline-5-carboxylate Chemical Properties
Melting point 51-52 °C(Solv: hexane (110-54-3))
Boiling point 315.1±15.0 °C(Predicted)
density 1.210±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka3.84±0.12(Predicted)
Safety Information
HS Code 2933499090
MSDS Information
Methyl quinoline-5-carboxylate Usage And Synthesis
Synthesis
Methanol

67-56-1

3-Aminobenzoic acid

99-05-8

Glycerol

56-81-5

Methyl quinoline-5-carboxylate

16675-62-0

Synthesis of methyl quinoline-5-carboxylate (Intermediate-97): To a 500 mL round-bottom flask equipped with a magnetic stirrer was added 90 mL of concentrated sulfuric acid solution of m-aminobenzoic acid (60 g, 435 mmol), glycerol (168 g, 1824 mmol) and 3-nitrobenzoic acid (30 g, 179 mmol). The reaction mixture was heated and stirred at 150°C for 7 hours. Upon completion of the reaction, the mixture was cooled to room temperature, methanol (600 mL) was added and refluxed for 12 hours. Subsequently, the mixture was cooled to 0°C, the reaction was quenched with ice water and concentrated under reduced pressure. The crude product was alkalized with aqueous sodium bicarbonate, extracted with dichloromethane and concentrated by combining the organic phases. The crude product was purified by silica gel column chromatography with the eluent being a solvent mixture of petroleum ether (60-80°C fraction), ethyl acetate and 0.5% triethylamine. Methyl quinoline-5-carboxylate (Intermediate-97) was finally obtained as a brown liquid (21 g).

References[1] Patent: WO2013/128465, 2013, A1. Location in patent: Page/Page column 203
[2] Patent: US2015/158860, 2015, A1. Location in patent: Paragraph 0750; 0751
Methyl quinoline-5-carboxylate Preparation Products And Raw materials
Raw materialsMethanol-->3-Aminobenzoic acid-->Glycerol
Tag:Methyl quinoline-5-carboxylate(16675-62-0) Related Product Information
Quinoline-5-carboxaldehyde Methyl quinoline-5-carboxylate Ethyl quinoline-5-carboxylate 5-Hydroxymethylquinoline Isoquinoline-5-carboxylic acid Quinoline-5-carboxylic acid