6931-16-4

Usage

Uses

Used in Chemical Synthesis:
2-Methoxyquinoline is used as a key intermediate in the synthesis of various organic compounds, particularly in the preparation of pharmaceuticals, agrochemicals, and other specialty chemicals. Its reactivity and functional group make it a valuable building block for the development of new molecules with potential applications.
Used in Catalysts:
2-Methoxyquinoline is used as a catalyst in enol oxidation reactions, specifically in the preparation of isopentenal. Its ability to facilitate the enol oxidation process enhances the efficiency and selectivity of the reaction, leading to improved yields and reduced side reactions.
Used in Method for Preparation:
2-Methoxyquinoline is employed in a method for the preparation of isopentenal through enol oxidation. This method leverages the catalytic properties of 2-Methoxyquinoline to achieve the desired product with high efficiency and selectivity, making it a preferred approach in the synthesis of isopentenal and related compounds.

InChI:InChI=1/C10H9NO/c1-12-10-7-6-8-4-2-3-5-9(8)11-10/h2-7H,1H3

Upstream product

• 612-62-4 2-Chloroquinoline 
• 3315-60-4 methanolate 
• 67-56-1 methanol 

Downstream Products

• 78941-89-6 2-oxo-1,2,3,4-tetrahydroquinoline-4-carboxylic acid methyl ester 
• 22297-12-7 α-(2-quinolyl)phenylacetonitrile 
• 59-31-4 2-hydroxyquinoline 
• 99455-05-7 2-methoxy-6-bromoquinoline 
• 146564-18-3 8-bromo-2-(methyloxy)quinoline 
• 886853-93-6 2-methoxy-3-quinolin-3-ylboronic acid 
• 1810-66-8 6-bromo-2-quinolone 
• 25932-48-3 N‐methyl‐N‐phenylquinolin‐2‐amine 
• 46708-03-6 2-(piperidin-1-yl)quinoline 
• 1609191-19-6 (S)-benzyl (1-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)-7-(methylamino)-7-oxoheptyl)carbamate 
• 1609191-18-5 (S)-7-(((benzyloxy)carbonyl)amino)-7-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)heptanoic acid 
• 1609191-17-4 (S)-tert-butyl 7-(((benzyloxy)carbonyl)amino)-7-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)heptanoate 
• 1609191-16-3 (S)-tert-butyl 7-(((benzyloxy)carbonyl)amino)-8-((2-(2-methoxyquinolin-3-yl)-2-oxoethyl)amino)-8-oxooctanoate 
• 16576-25-3 2-benzoylquinoline 

Relevant academic research and scientific papers

Tetramethylammonium Fluoride Alcohol Adducts for SNAr Fluorination

Nucleophilic aromatic fluorination (SNAr) is among the most common methods for the formation of C(sp2)-F bonds. Despite many recent advances, a long-standing limitation of these transformations is the requirement for rigorously dry, aprotic conditions to maintain the nucleophilicity of fluoride and suppress the generation of side products. This report addresses this challenge by leveraging tetramethylammonium fluoride alcohol adducts (Me4NF·ROH) as fluoride sources for SNAr fluorination. Through systematic tuning of the alcohol substituent (R), tetramethylammonium fluoride tert-amyl alcohol (Me4NF·t-AmylOH) was identified as an inexpensive, practical, and bench-stable reagent for SNAr fluorination under mild and convenient conditions (80 °C in DMSO, without the requirement for drying of reagents or solvent). A substrate scope of more than 50 (hetero) aryl halides and nitroarene electrophiles is demonstrated.

Hydrogen Atom Transfer Oxidation of Primary and Secondary Alcoholates into Aldehydes and Ketones by Aromatic Halides in Liquid Ammonia. A New Electrochemically Induceable Reaction

It is possible to induce the oxidation of alcoholates into the corresponding carbonyl compounds by electrochemical reduction of aromatic halides in liquid ammonia, i.e., to electrochemically trigger the reaction ArX + >CH-O- -> ArH + >C=O + X-.H-Atom transfer from the acoholate to the aryl radical formed upon reduction of the aryl halide appears as the key step of the oxidation process.The ketyl anion radical thus formed can be oxidized into the parent carbonyl compound, remain electrochemically stable, or be reduced into the dianion depending upon the location of the two corresponding standard potentials toward the reduction potential of the aryl halide.Electricity consumption thus tends toward 0, 1, and 2 F/mol for the three cases, respectively.The reactions competing with H-atom transfer, thus lowering the efficiency of the electrochemical inducement of the oxidation process, are electron transfer to the aryl radical which occur at the electrode surface and/or in the solution.These will play the role of termination steps for the corresponding chain system involving homogeneous initiation of the reaction.The kinetic analysis of the competition between H-atom transfer and homogeneous or heterogeneous electron transfer allows a detailed investigation of the reaction mechanism by electrochemical techniques such as cyclic voltammetry.This also leads to the determination of the rate constants of H-atom transfer of the alcoholate-aryl radical couple.