10447-29-7

Basic information

• Product Name: Ethyl quinoline-4-carboxylate
• Synonyms: Ethyl quinoline-4-carboxylate;4-Quinolinecarboxylic acid, ethyl ester
• CAS NO: 10447-29-7
• Molecular Formula: C₁₂H₁₁NO₂
• Molecular Weight: 201.224
• Mol File: 10447-29-7.mol

Chemical Properties

• Melting Point: 155-157 °C(Solv: benzene (71-43-2))
• Boiling Point: 317.3°Cat760mmHg
• Flash Point: 145.7°C
• Appearance: /
• Density: 1.175g/cm³
• Vapor Pressure: 0.000388mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.88±0.13(Predicted)
• CAS DataBase Reference: Ethyl quinoline-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl quinoline-4-carboxylate(10447-29-7)
• EPA Substance Registry System: Ethyl quinoline-4-carboxylate(10447-29-7)

Safety Data

• Hazardous Substances Data: 10447-29-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl quinoline-4-carboxylate is used as a building block for the synthesis of pharmaceuticals. Its role in creating new drugs is significant due to its chemical reactivity and the biological activities it can impart to the final products.
Used in Agrochemical Industry:
In the agrochemical sector, ethyl quinoline-4-carboxylate is utilized as a key component in the development of agrochemicals. Its incorporation can lead to the creation of more effective pesticides and other agricultural chemicals.
Used in Organic Chemistry:
Ethyl quinoline-4-carboxylate is used as a versatile intermediate in organic synthesis. Its presence in the synthesis process can facilitate the creation of a wide range of organic compounds with diverse applications.
Used in Flavor and Fragrance Industry:
Ethyl quinoline-4-carboxylate is used as a contributor to the aroma of certain compounds in the flavor and fragrance industry. Its ability to enhance or create specific scents makes it a valuable asset in the creation of perfumes, food flavorings, and other aromatic products.
Used in Biological Research:
Ethyl quinoline-4-carboxylate is used in biological research for its antitumor, antibacterial, and antifungal properties. These activities make it a subject of interest for scientists exploring new treatments and therapies in medicine.

InChI:InChI=1/C12H11NO2/c1-2-15-12(14)10-7-8-13-11-6-4-3-5-9(10)11/h3-8H,2H2,1H3

Upstream product

• 2973-27-5 quinoline-4-carbonitrile 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 91-22-5 quinoline 
• 50821-72-2 quinolone-4-carbonyl chloride 
• 64-17-5 ethanol 
• 56-57-5 4-nitroquinoline-N-oxide 
• 15733-89-8 2-hydroxyquinoline-4-carboxylic acid 
• 5467-57-2 2-chloroquinoline-4-carboxylic acid 
• 69564-74-5 1-vinylindoline-2,3-dione 
• 91-56-5 indole-2,3-dione 
• 5467-61-8 ethyl ester of 2-chlorocinchoninic acid 
• 855166-61-9 2-iodo-quinoline-4-carboxylic acid 
• 5323-57-9 quinoline-2,4-dicarboxylic acid 
• 3964-04-3 4-bromoquinoline 

Downstream Products

• 109646-41-5 quinoline-4-carboxylic acid-(2-benzo[1,3]dioxol-5-yl-1-methyl-ethylamide) 
• 54885-00-6 phenyl(quinolin-4-yl)methanone 
• 106473-25-0 3-[4]quinolyl-3-oxo-propionic acid ethyl ester 
• 83629-96-3 1-(quinolin-4-yl)propan-1-one 
• 56153-32-3 4-ethoxycarbonyl-1-methyl-quinolinium; iodide 
• 855605-82-2 1-[4]quinolyl-2-phenyl-ethanone 
• 6281-32-9 4-quinolylmethanol 
• 4363-95-5 quinoline-4-carboxamide 
• 29620-62-0 cinchoninic hydrazide 
• 24562-76-3 Ethyl 1,2,3,4-tetrahydroquinoline-4-carboxylate 
• 83255-81-6 ethyl 2-cyclohexyl-4-quinolinecarboxylate 
• 110435-99-9 diphenyl(quinolin-4-yl)methanol 

Relevant articles and documents

Synthesis of Quinoline-4-carboxamides and Quinoline-4-carboxylates via a Modified Pfitzinger Reaction of N-Vinylisatins

A synthetic approach for the accelerated assembly of quinoline-4-carboxamide and quinoline-4-carboxylate nuclei is presented. The methodology is based on the rearrangement of N-vinylisatins promoted by different types of amines (or ethanol) in a Pfitzinger-type mechanism that, in turn, builds the quinoline ring system. The reaction took place only by heating the starting materials in ethanol, without any additive.

SYNTHESIS OF QUINOLINE-4-CARBOXYLIC ACID AND ITS DERIVATIVES

2-Methylquinoline-4-carboxylic acid was obtained by the reaction of isatin with acetone in the presence of alkali.This acid was converted through a step involving (E)-2-styrylquinoline-4-carboxylic acid to quinoline-2,4-dicarboxylic acid, from which quinoline-4-carboxylic acid was obtained by refluxing in nitrobenzene.The structures of the synthesized compounds were confirmed by 1H NMR spectroscopy using two-dimensional (2DJ) spectra.

Photochemical Reaction of Ethoxycarbonyl-Substituted Quinolines

The photochemical reactions of the quinoline derivatives substituted by an ethoxycarbonyl group at the 2-, 3-, and 4-positions of a quinoline nucleus have been investigated in several alcohols and cyclohexane.Irradiation of ethyl 4-quinolinecarboxylate (1) yielded ethyl 2-hydroxyalkyl-4-quinolinecarboxylates (4a-c) in alcohols and ethyl 2-cyclohexyl-4-quinolinecarboxylate (4d) in cyclohexane in a good yield, respectively.The photochemical reactions of ethyl 3-quinolinecarboxylate (2) showed remarkable solvent dependency.Irradiation in methanol and cyclohexane afforded a solvent-additive product, ethyl 4-hydroxymethyl-1,4-dihydro-3-quinolinecarboxylate (5a) and ethyl 4-cyclohexyl-1,4-dihydro-3-quinolinecarboxylate (5b), while such photoaddition of the solvent did not proceed in ethanol and 2-propanol but instead ethyl 1,4-dihydro-3-quinolinecarboxylate (6) and dimeric compounds were formed, both of which were unstable and finally reverted to 2 at room temperature in air.In the case of ethyl 2-quinolinecarboxylate two types of the products, ethyl 4-hydroxyalkyl-1,4-dihydro-2-quinolinecarboxylate (7) and ethyl 1,4-dihydro-2-quinolinecarboxylate (8) were obtained in ethanol and 2-propanol but the yields of those products were poor.On the basis of triplet quenching experiments, the photochemical reactions of those ethyl quinolinecarboxylates are suggested to occur through hydrogen abstraction from the solvents by the ring nitrogen in the S1 state.

HOMOLYTIC ALKOXYCARBONYLATION REACTIONS IN TWO-PHASE SYSTEMS, PART II. STUDIES ON THE ETHOXYCARBONYLATION OF SOME SELECTED ?-DEFICIENT N-HETEROAROMATIC SYSTEMS

A systematic study on the homolytic substitution of pyridine, quinoline and pyrazine by ethoxycarbonyl radicals was performed.It is demonstrated that under appropriate conditions Minisci-type alkoxycarbonylation reactions can provide convenient access to heteroaromatic monocarboxylic acid esters, like alkyl 2-pyrazinecarboxylates and alkyl 4-alkyl-2-pyridinecarboxylates.