ChemicalBook--->CAS DataBase List--->53951-84-1

53951-84-1

53951-84-1 Structure

53951-84-1 Structure
IdentificationBack Directory
[Name]

methyl quinoline-3-carboxylate
[CAS]

53951-84-1
[Synonyms]

Methyl 3-quinolinecarboxylate
methyl quinoline-3-carboxylate
3-Quinolinecarboxylic acid, methyl ester
Quinoline-3-carboxylic acid methyl ester
[Molecular Formula]

C11H9NO2
[MDL Number]

MFCD03550859
[MOL File]

53951-84-1.mol
[Molecular Weight]

187.19
Chemical PropertiesBack Directory
[Melting point ]

73-74 °C
[Boiling point ]

294.5±13.0 °C(Predicted)
[density ]

1.210±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Room Temperature
[pka]

3.11±0.11(Predicted)
[Appearance]

Off-white to light yellow Solid
Safety DataBack Directory
[HS Code ]

2933499090
Hazard InformationBack Directory
[Synthesis Reference(s)]

Journal of Medicinal Chemistry, 25, p. 1081, 1982 DOI: 10.1021/jm00351a015
[Synthesis]

Methanol

67-56-1

3-Quinolinecarboxylic acid

6480-68-8

methyl quinoline-3-carboxylate

53951-84-1

General procedure for the synthesis of methyl 3-quinolinecarboxylate from methanol and quinoline-3-carboxylic acid: quinoline-3-carboxylic acid (3 g, 17.32 mmol) was dissolved in methanol (30 mL) and cooled at 0°C in an ice bath. Subsequently, thionyl chloride (1.264 mL, 17.32 mmol) was added slowly and dropwise, then the reaction mixture was heated to 80°C and kept overnight. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the methanol was evaporated under reduced pressure and the resulting residue was alkalized with saturated sodium bicarbonate solution to pH 7 to 8, precipitating a white solid. After filtration and drying, methyl 3-quinolinecarboxylate (3.2 g, 99% yield) was obtained as a white solid; mass spectrometry (M/Z) showed a molecular ion peak of 187.3.

[References]

[1] Patent: WO2014/33604, 2014, A1. Location in patent: Page/Page column 48
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 24, p. 5505 - 5510
[3] Tetrahedron Asymmetry, 2013, vol. 24, # 18, p. 1142 - 1147
[4] Patent: US2016/122303, 2016, A1. Location in patent: Paragraph 0078
[5] Tetrahedron Asymmetry, 2010, vol. 21, # 18, p. 2307 - 2313
Spectrum DetailBack Directory
[Spectrum Detail]

methyl quinoline-3-carboxylate(53951-84-1)1HNMR
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