612-61-3

Usage

Uses

Used in Pharmaceutical Industry:
7-CHLOROQUINOLINE is used as an antimicrobial agent for combating antibiotic-resistant bacteria, specifically Enterobacter aerogenes isolates. Its ability to block antibiotic efflux pumps helps in overcoming resistance and enhancing the effectiveness of antibiotics.
Used in Research and Development:
7-CHLOROQUINOLINE serves as a valuable compound in the development of new strategies to combat antibiotic resistance. Its chemical properties make it a promising candidate for further research and the creation of novel treatments for various bacterial infections.
Used in Quality Control and Testing:
In the field of microbiology and pharmaceutical quality control, 7-CHLOROQUINOLINE can be utilized as a reference compound to test the susceptibility of antibiotic-resistant bacteria to new or existing treatments. This helps in evaluating the effectiveness of antibiotics and the potential for resistance development.

InChI:InChI=1/C9H6ClN/c10-8-4-3-7-2-1-5-11-9(7)6-8/h1-6H

Upstream product

• 108-42-9 3-chloro-aniline 
• 56-81-5 glycerol 
• 1375234-69-7 3-(2-amino-4-chlorophenyl)-2-propyn-1-ol 
• 1060737-02-1 3-(2-amino-4-chlorophenyl)-propan-1-ol 
• 6828-35-9 5-chloro-2-iodoaniline 
• 98591-57-2 7-chloro-4-iodoquinoline 
• 100-52-7 benzaldehyde 
• 504-63-2 trimethyleneglycol 
• 1203646-03-0 7-chloro-4-quinolinyltriphenylphosphonium iodide 
• 86-98-6 4,7-dichloroquinoline 
• 201230-82-2 carbon monoxide 
• 98-80-6 phenylboronic acid 
• 3820-67-5 glafenine 
• 93626-92-7 (2E)-3-(4-chlorophenyl)acrylaldehyde O-methyl oxime 

Downstream Products

• 66293-57-0 1-benzoyl-7-chloro-1,2-dihydro-quinoline-2-carbonitrile 
• 89770-32-1 N,N-dimethylquinolin-7-amine 
• 71331-02-7 7-chloro-8-nitroquinoline 
• 6338-98-3 7-chloro-[8]quinolylamine 
• 90562-35-9 7-chloro-1,2,3,4-tetrahydroquinoline 
• 854018-72-7 7-chloro-4-(2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-quinoline 
• 67360-38-7 quinoline-7-carbonitrile 
• 889936-67-8 C₁₅H₁₀FN 
• 1182846-73-6 C₁₆H₁₃N 
• 61687-26-1 7-chloro-2-phenyl-quinoline 
• 1182846-72-5 C₁₆H₁₀F₃N 
• 1182846-77-0 C₁₇H₁₁N 
• 1182846-71-4 C₁₈H₁₇NO₃ 
• 29314-09-8 7-phenylquinoline 

Relevant academic research and scientific papers

Synthesis of 7-Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents

We have prepared a library of functionalized quinolines through the magnesiation of 7-chloroquinolines under mild conditions, employing both batch and continuous flow conditions. The preparation involved the generation of mixed lithium-magnesium intermediates, which were reacted with different electrophiles. Mixed lithium-zinc reagents allowed the synthesis of halogenated and arylated derivatives. Some of the synthesized 4-carbinol quinolines have shown interesting antiproliferative properties, their hydroxyl group being a suitable amino group bioisostere. We also report a two-step approach for optically active derivatives.

Synthesis of quinolines by iron-catalyzed reaction of anilines with propane-1,3-diol

Quinoline and its derivatives were synthesized by cyclocondensation of anilines with propane-1,3-diol in 57-96% yield in the presence of iron-containing catalysts in carbon tetrachloride.

The synthesis of N-heterocycles via copper/TEMPO catalysed aerobic oxidation of amino alcohols

N-Heterocycles can be prepared using alcohol oxidation as a key synthetic step. Herein we report studies exploring the potential of Cu/TEMPO as an aerobic oxidation catalyst for the synthesis of substituted indoles and quinolines.

The selective deiodination of iodoheterocycles using the PhSiH3 - In(OAc)3 system

Nitrogen-containing π-deficient heterocyclic iodides such as iodoquinolines or iodopyridines were deiodinated by treatment with phenylsilane catalyzed by indium acetate to give the corresponding deiodinated heterocycles at ambient temperature.

Hydrodehalogenation of halogenated pyridines and quinolines by sodium borohydride/N,N,N′,N′-tetramethylethylenediamine under palladium catalysis

A protocol for the hydrodehalogenation of halogenated pyridines and quinolines by the sodium borohydride/N,N,N′,N′-tetramethylethylenediamine (NaBH4-TMEDA) system under palladium catalysts is reported. Catalytic amounts of [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium(II) in combination with NaBH4-TMEDA rapidly hydrodehalogenate chloro(bromo)-pyridines and -quinolines at room temperature in quantitative yields. Chemoselective reduction of 4,7-dichloroquinoline affords 7-chloroquinoline as the sole product in almost quantitative yield. Moreover, palladium(II) acetate-triphenylphosphine and NaBH4-TMEDA are able to reduce efficiently reactive bromo-pyridines and -quinolines.

7-Chloroquinoline: a versatile intermediate for the synthesis of 7-substituted quinolines

A practical synthesis of 7-mono-substituted quinolines has been achieved. Selective reduction of the inexpensive commercial reagent 4,7-dichloroquinoline affords 7-chloroquinoline, which has been converted into more complex 7-mono-substituted quinolines through a series of Pd-catalyzed cross coupling reactions. These studies include the first examples of Suzuki reactions for the preparation of 7-mono-substituted quinolines as well as the first application of the Sonagashira reaction for the synthesis of 7-substituted quinolines. This strategy has been extended to the preparation of 2,7-di-substituted quinolines.

Chemistry of heteroaryltriphenylphosphonium iodides: Preparation from iodoheteroaromatics and elimination of the phosphonium iodide group using basic solvents

α- and γ-Iodoheteroaromatics were found to react with triphenylphosphine to give heteroaromatictriphenylphosphonium iodides in excellent yields, β-lodoheteroaromatics, which are less reactive with triphenylphosphine compared to α- or γ-compounds, were con

Direct Synthesis of Benzoylpyridines from Chloropyridines via a Palladium-Carbene Catalyzed Carbonylative Suzuki Cross-Coupling Reaction

The use of N-heterocyclic carbene-type ligands with palladium catalysts allows the activation of chloropyridines and chloroquinoline towards carbonylative cross-coupling with phenylboronic acid for the synthesis of unsymmetrical biaryl ketones.

Photochemical degradation of glaphenine solution

The aim of this work was to study the effect of light on glaphenine stability in solutions. Glaphenine solutions in various solvents, including alcohols, acidic alcohols, water and acidic aqueous media, were exposed to both artificial light source and solar radiation. The photodegradation was followed using different techniques including UV-visible spectrophotometry, spectrofluorometry, mass spectrometry, HPLC and TLC. Studying the effect of solvents on the stability showed that glaphenine is completely stable towards light in water and in acidic media. In neutral alcohols, the rate of photodecomposition was found to increase in the order methanol ethanol pentanol butanol propanol, which may be explained by solvent-solute interaction and viscous properties of the solvent. Two photodegraded products were separated and identified as α-glycerylanthranilate and 7-chloroquinoline.

Thermolysis of Polyazapentadienes. Part 7. An Unambiguous Route to 7-Substituted Quinolines from Cinnamaldehyde Derivatives

Flash vacuum pyrolysis of the cinnamaldehyde phenylhydrazone derivatives (4) - (6) or O-alkyl oxime derivatives (7) - (12) at 600 -650 deg C and 10-2 - 10-3 Torr leads to approximately equal quantities of cinnamonitriles and quinolines.Use of a p-substituted cinnamaldehyde derivatives gives the appropriate 7-substituted quinoline in high isomeric purity; the reactions take place via conjugated iminyl radicals.