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ChemicalBook--->CAS DataBase List--->24195-07-1

24195-07-1

24195-07-1 Structure

24195-07-1 Structure
IdentificationBack Directory
[Name]

quinolinic acid, 2-methyl ester
[CAS]

24195-07-1
[Synonyms]

QA2ME
2-Methyl quinolinate
2-carbomethoxynicotinic acid
quinolinic acid, 2-methyl ester
2-(methoxycarbonyl)nicotinic acid
2-methoxycarbonyl-3-pyridinecarboxylic acid
2-Methoxycarbonylpyridine-3-carboxylic acid
2,3-Pyridinedicarboxylic acid, 2-methyl ester
[Molecular Formula]

C8H7NO4
[MDL Number]

MFCD00111560
[MOL File]

24195-07-1.mol
[Molecular Weight]

181.15
Chemical PropertiesBack Directory
[Melting point ]

54-55 °C
[Boiling point ]

380.7±27.0 °C(Predicted)
[density ]

1.361±0.06 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,Room Temperature
[pka]

2.59±0.10(Predicted)
[Appearance]

White to off-white Solid
[InChI]

InChI=1S/C8H7NO4/c1-13-8(12)6-5(7(10)11)3-2-4-9-6/h2-4H,1H3,(H,10,11)
[InChIKey]

OSSIORZYXTUXBL-UHFFFAOYSA-N
[SMILES]

C1(C(OC)=O)=NC=CC=C1C(O)=O
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[HS Code ]

2933399990
Spectrum DetailBack Directory
[Spectrum Detail]

quinolinic acid, 2-methyl ester(24195-07-1)1HNMR
Hazard InformationBack Directory
[Synthesis]

Methanol

67-56-1

2,3-Pyridinedicarboxylic anhydride

699-98-9

quinolinic acid, 2-methyl ester

24195-07-1

General procedure for the synthesis of methyl 3-carboxylic acid pyridine-2-carboxylate from methanol and 2,3-pyridinedicarboxylic anhydride: 2,3-pyridinedicarboxylic anhydride (5.0 g, 34 mmol) was dissolved in methanol (25 mL). The reaction mixture was heated to reflux for 2 hours and the solvent was subsequently removed by rotary evaporation. The resulting white solid was dissolved in ethyl acetate (25 mL) under reflux conditions and the insoluble by-products were removed by filtration. The filtrate was concentrated under reduced pressure and recrystallized from ethyl acetate to give the final methyl 3-carboxypyridine-2-carboxylate (4.5 g, 71% yield) as a white solid with a melting point of 157-159 °C.1H NMR (300 MHz, CDCl3) δ 8.84 (dd, J=1.7,5.0 Hz, 1H), 8.34 (dd, J=1.6, 7.9 Hz, 1H), 7.57 (dd, J=5.0,8.1 Hz, 1H), 4.00 (s, 3H).

[References]

[1] Angewandte Chemie - International Edition, 2011, vol. 50, # 22, p. 5192 - 5196
[2] Synlett, 2006, # 12, p. 1938 - 1942
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 8, p. 3840 - 3853
[4] Patent: WO2017/160898, 2017, A1. Location in patent: Paragraph 00107; 00136
[5] Journal of Medicinal Chemistry, 2006, vol. 49, # 15, p. 4544 - 4567
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