5965-59-3

Basic information

• Product Name: Methyl 4-Hydroxyquinoline-2-carboxylate
• Synonyms: Methyl 4-Hydroxyquinoline-2-carboxylate;Methyl 4-hydroxy-2-quinolinecarboxylate;Methyl 4-hydroxyquinaldinate;Methyl kynurenate;Kynurenic acid, methyl ester;methyl 4-oxo-1H-quinoline-2-carboxylate
• CAS NO: 5965-59-3
• Molecular Formula: C₁₁H₉NO₃
• Molecular Weight: 203.2
• Mol File: 5965-59-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 224 °C
• Boiling Point: 331.1 °C at 760 mmHg
• Flash Point: 154 °C
• Appearance: /
• Density: 1.288 g/cm³
• Vapor Pressure: 0.00016mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.53±0.40(Predicted)
• CAS DataBase Reference: Methyl 4-Hydroxyquinoline-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-Hydroxyquinoline-2-carboxylate(5965-59-3)
• EPA Substance Registry System: Methyl 4-Hydroxyquinoline-2-carboxylate(5965-59-3)

Safety Data

• Hazardous Substances Data: 5965-59-3(Hazardous Substances Data)

Usage

Description

Methyl 4-hydroxyquinoline-2-carboxylate is an organic compound with the molecular formula C10H9NO3. It is a derivative of quinoline, featuring a hydroxyl group and a carboxylate group attached to the quinoline ring. Methyl 4-hydroxyquinoline-2-carboxylate is known for its potential applications in various fields due to its unique chemical structure and properties.

Uses

Used in Pharmaceutical Industry:
Methyl 4-hydroxyquinoline-2-carboxylate is used as a key intermediate in the synthesis of macro-heterocyclic compounds. These compounds have been identified as potential inhibitors of blood coagulation factor XIa, which plays a crucial role in the coagulation cascade. By inhibiting factor XIa, these macro-heterocyclic compounds can help regulate blood clotting and may be useful in the development of novel therapeutics for conditions related to abnormal blood clotting, such as deep vein thrombosis and stroke.

InChI:InChI=1/C11H9NO3/c1-15-11(14)9-6-10(13)7-4-2-3-5-8(7)12-9/h2-6H,1H3,(H,12,13)

Upstream product

• 67-56-1 methanol 
• 492-27-3 kinurenic acid 
• 62-53-3 aniline 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 4916-29-4 dimethyl 2-(phenyl-amino)-2-butendioate 
• 13593-94-7 kynurenic acid 
• 86119-84-8 phosphoric acid 
• 25007-54-9 Dimethyl 2-oxosuccinate 
• 553-90-2 Dimethyl oxalate 
• 551-93-9 2-aminoacetophenone 
• 10567-58-5 dimethyl 2-(phenylamino)maleate 
• 4916-29-4 dimethyl (Z)-N-(phenyl)aminofumarate 
• 186581-53-3 diazomethane 

Downstream Products

• 13593-94-7 kynurenic acid 
• 139896-91-6 methyl 4-bromoquinoline-2-carboxylate 
• 1258962-35-4 methyl 1-benzoyl-4-oxo-1,4-dihydro-quinoline-2-carboxylate 
• 1258962-36-5 methyl 1-(4'-methylbenzoyl)-4-oxo-1,4-dihydroquinoline-2-carboxylate 
• 1258962-37-6 methyl 1-(4'-chlorobenzoyl)-4-oxo-1,4-dihydroquinoline-2-carboyxlate 
• 1354965-46-0 C₁₈H₁₂N₄O₂ 
• 1354965-44-8 C₁₉H₁₄N₄O₂ 
• 15733-83-2 4-methoxyquinoline-2-carboxylic acid 
• 798576-75-7 4-benzyloxyquinoline-2-carboxylic acid [1(S)-(3,4-dibenzyloxy-5-oxo-2,5-dihydrofuran-2(R)-yl)-2-bromoethyl] ester 
• 102028-50-2 methyl 4-(benzyloxy)quinoline-2-carboxylate 
• 97909-55-2 methyl-4-aminoquinoline-2-carboxylate 
• 97909-67-6 4-[(E)-4-Chloro-phenoxysulfonylimino]-1,4-dihydro-quinoline-2-carboxylic acid methyl ester 
• 97927-34-9 4-[(E)-Toluene-4-sulfonylimino]-1,4-dihydro-quinoline-2-carboxylic acid methyl ester 

Relevant articles and documents

Synthesis of Natural and Unnatural Quinolones Inhibiting the Growth and Motility of Bacteria

Synthesis of a recently discovered S-methylated quinolone natural product (1) was carried out, in addition to the production of a range of 2-substituted 4-quinolone derivatives (2-11). Two approaches were used: (i) the base-catalyzed cyclization of N-(ket

Photoreductive Removal of O-Benzyl Groups from Oxyarene N-Heterocycles Assisted by O-Pyridine-pyridone Tautomerism

Facile photoreductive protocols have been developed to remove benzyl O-protective groups from oxyarene N-heterocycles at positions capable for 2-/4-O-pyridine-2-/4-pyridone tautomerism. Blue light irradiation, a [Ru] or [Ir] photocatalyst, and ascorbic acid in a water-acetonitrile solution debenzylates a variety of aryl N-heterocycles cleanly and selectively. Ascorbic acid has two functions in the reaction. On the one hand, it protonates the N-heterocycles that reduces their reduction potentials notably and on the other hand it acts as a sacrificial reductant. Reduction potentials and free energy barriers calculated at the CPCM-B3LYP/6-31+G? level can predict the reactivities of the studied substrates.

The synthesis of quinolone natural products from pseudonocardia sp.

The synthesis of four quinolone natural products from the actinomycete Pseudonocardia sp. is reported. The key step involved a sp2-sp3 Suzuki-Miyaura reaction between a common boronic ester lateral chain and various functionalised quinolone cores. The quinolones slowed growth of E. coli and S. aureus by inducing extended lag phases. The total synthesis of four quinolone natural products is reported. The quinolones were synthesised in a highly efficient and direct manner from various readily prepared quinolone cores and a common boronic ester lateral chain. The key step involved a challenging sp2-sp3 Suzuki-Miyaura reaction.