Identification | Back 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 Properties | Back 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 |
Hazard Information | Back Directory | [Synthesis]
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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Energy Chemical
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