27805-12-5

Basic information

• Product Name: 3-Pyridinecarboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester
• Synonyms: 3-Pyridinecarboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester;ethyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile;ETHYL 2-HYDROXYPYRIDINE-3-CARBOXYLATE;2-Oxo-1,2-dihydro-pyridine-3-carboxylic acid ethyl ester;2-Oxo-1,2-dihydro-pyridine-3-carboxylic acid tert-butyl ester;Ethyl 2-oxo-1,2-dihydropyridine-3-carboxylate
• CAS NO: 27805-12-5
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16
• Mol File: 27805-12-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 369.661°C at 760 mmHg
• Flash Point: 177.365°C
• Appearance: /
• Density: 1.214g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.512
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 3-Pyridinecarboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridinecarboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester(27805-12-5)
• EPA Substance Registry System: 3-Pyridinecarboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester(27805-12-5)

Safety Data

• Hazardous Substances Data: 27805-12-5(Hazardous Substances Data)

Usage

General Description

3-Pyridinecarboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester is a chemical compound, also recognized as Ethyl 2-oxo-1,2-dihydropyridine-3-carboxylate. It belongs to the class of chemicals known as pyridinecarboxylic acids, specifically esters of such acids. Being an ester, it's a product of condensation between an acid and an alcohol. Its molecular formula is C9H9NO3 and it's commonly used in organic synthesis. As with many esters, it likely has a fruity or sweet scent. As with all chemicals, appropriate safety and handling procedures must be followed due to potential hazards associated with its use.

InChI:InChI=1/C8H9NO3/c1-2-12-8(11)6-4-3-5-9-7(6)10/h3-5H,2H2,1H3,(H,9,10)

Upstream product

• 609-71-2 2-hydroxy-3-carboxypyridine 
• 64-17-5 ethanol 
• 609-71-2 1,2-dihydro-2-oxonicotinic acid 
• 17758-13-3 1-phenyl-2(1H)-pyrimidinone 
• 105-53-3 diethyl malonate 
• 17758-14-4 1-p-tolylpyrimidin-2(1H)-one 
• 20577-27-9 2-hydroxy-3-cyanopyridine 
• 110-89-4 piperidine 
• 28369-76-8 2-hydroxynicotinic acid chloride 

Downstream Products

• 153336-74-4 2-hydroxynicotinohydrazide 
• 16498-79-6 ethyl 2-methoxynicotinate 
• 15506-19-1 1-Methyl-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid ethyl ester 
• 10128-92-4 1,2-dihydro-2-oxopyridine-3-carboxamide 

Relevant articles and documents

ISOINDOLINONE DERIVATIVES AS IRAK4 MODULATORS

Compounds of Formula (0), and stereoisomers and pharmaceutically acceptable salts thereof, as well as methods of use as Interleukin-1 Receptor Associated Kinase (IRAK4) inhibitors are described herein.

Potent antimicrobial agents against azole-resistant fungi based on pyridinohydrazide and hydrazomethylpyridine structural motifs

Abstract Schiff base derivatives have recently been shown to possess antimicrobial activity, and these derivatives include a limited number of salicylaldehyde hydrazones. To further explore this structure-activity relationship between salicylaldehyde hydrazones and antifungal activity, we previously synthesized and analyzed a large series of salicylaldehyde and formylpyridinetrione hydrazones for their ability to inhibit fungal growth of both azole-susceptible and azole-resistant species of Candida. While many of these analogs showed excellent growth inhibition with low mammalian cell toxicity, their activity did not extend to azole-resistant species of Candida. To further dissect the structural features necessary to inhibit azole-resistant fungal species, we synthesized a new class of modified salicylaldehyde derivatives and subsequently identified a series of modified pyridine-based hydrazones that had potent fungicidal antifungal activity against multiple Candida spp. Here we would like to present our synthetic procedures as well as the results from fungal growth inhibition assays, mammalian cell toxicity assays, time-kill assays and synergy studies of these novel pyridine-based hydrazones on both azole-susceptible and azole-resistant fungal species.

Role of lactam vs. lactim tautomers in 2(1H)-pyridone catalysis of aromatic nucleophilic substitution

3-Ethylaminocarbonyl-2(1H)-pyridone 1 and 3-ethoxycarbonyl-2(1H)-pyridone 2 have been synthesised and tested as catalysts for the aromatic nucleophilic substitution of fluoride by piperidine in 2-fluoro-5-nitrobenzonitrile 3. A kinetic model which takes into account the dimerisation of the catalysts has been developed, which allows a quantitative analysis of measured data. 3-Ethylaminocarbonyl-2(1H)-pyridone 1 exists exclusively as a lactam tautomer, either monomeric or dimeric but 3-ethoxycarbonyl-2(1H)-pyridone 2 exists as a lactim monomer, whereas its dimer exists in the lactam form. Despite such differences, these two compounds exhibit similar catalytic efficiencies for the reaction studied, suggesting that lactim and lactam tautomers have comparable efficiencies in tautomeric catalysis.