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Usage

Uses

Used in Pharmaceutical Industry:
2-Chloroquinoline is used as an intermediate in the synthesis of various compounds, particularly those with antifungal properties. It plays a crucial role in the development of new drugs to combat fungal infections.
Used in Organic Synthesis:
2-Chloroquinoline serves as an important raw material and intermediate in organic synthesis, where it is utilized to create a variety of chemical compounds with diverse applications.
Used in Agrochemicals:
In the agrochemical industry, 2-Chloroquinoline is employed as a key intermediate for the production of various pesticides and other agricultural chemicals, contributing to the development of more effective and environmentally friendly products.
Used in Dye Industry:
2-Chloroquinoline is also used as an intermediate in the synthesis of dyes, where its unique chemical properties enable the creation of a wide range of colors and pigments for various applications.
Used in Cytotoxic DNA Topoisomerase II Inhibitors:
2-Chloroquinoline is used as a starting material in the synthesis of novel cytotoxic DNA topoisomerase II inhibitors. It reacts with benzotriazole and undergoes cyclization with the loss of nitrogen, resulting in the formation of the indolo[2,3-b]quinoline ring system, which is essential for the development of these inhibitors. These inhibitors have potential applications in cancer treatment, as they can interfere with the replication and transcription of DNA in cancer cells, thereby inhibiting their growth and proliferation.

Synthesis Reference(s)

The Journal of Organic Chemistry, 67, p. 7884, 2002 DOI: 10.1021/jo016196iSynthesis, p. 1013, 1987 DOI: 10.1055/s-1987-28152

Purification Methods

Purify it by crystallisation of its picrate to constant melting point (123-124o) from *benzene, regenerating the base and distilling it under vacuum [Cumper et al. J Chem Soc 1183 1962]. 2-Chloroquinoline can be crystallised from EtOH. Its picrate has m 123-124o (from EtOH). [Beilstein 20 H 359, 20/7 V 312.]

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

Upstream product

• 75-44-5 phosgene 
• 606-43-9 1-methyl-2-quinolin-2(1H)-one 
• 108-88-3 toluene 
• 59-31-4 2-quinolone 
• 6560-83-4 2-iodoquinoline 
• 2423-68-9 2-Chloroquinoline 1-oxide 
• 67-66-3 chloroform 
• 121-69-7 N,N-dimethyl-aniline 
• 100-61-8 N-methylaniline 
• 90-14-2 1-Iodonaphthalene 
• 90-13-1 1-Chloronaphthalene 
• 1613-37-2 Quinoline N-oxide 
• 98-88-4 benzoyl chloride 
• 100-47-0 benzonitrile 

Downstream Products

• 46708-03-6 2-(piperidin-1-yl)quinoline 
• 4774-24-7 2-(piperazin-1-yl)quinoline 
• 23165-19-7 4,4-dimethylmorpholinium chloride 
• 64495-58-5 2-benzenesulfonyl-quinoline 
• 1436-43-7 quinoline-2-carbonitrile 
• 40515-82-0 2-(2-quinolinyl)phenol 
• 22190-12-1 2-phenylsulfanyl-quinoline 
• 116249-87-7 benzyl 2-quinolyl sulfide 
• 5468-85-9 N-phenylquinolin-2-amine 
• 22297-12-7 α-(2-quinolyl)phenylacetonitrile 
• 94538-48-4 (2-methoxy-phenyl)-quinolin-2-yl-amine 
• 4800-58-2 1-ethyl-2-iodoquinolinium iodide 
• 2637-37-8 Quinoline-2-thiol 
• 2637-37-8 Quinoline-2-thione 

Relevant academic research and scientific papers

Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis

The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.

Transition-metal-free decarboxylative halogenation of 2-picolinic acids with dihalomethane under oxygen conditions

A convenient and efficient method for the synthesis of 2-halogen-substituted pyridines is described. The decarboxylative halogenation of 2-picolinic acids with dihalomethane proceeded smoothly via N-chlorocarbene intermediates to afford 2-halogen-substituted pyridines in satisfactory to excellent yields under transition-metal-free conditions. This new type of decarboxylative halogenation is operationally simple and exhibits high functional-group tolerance.

Environment-friendly preparation method of 2-chloroquinoline

The invention discloses an environment-friendly preparation method of 2-chloroquinoline. The method comprises the following steps: dissolving quinoline N-oxide as a raw material in a certain amount ofa solvent, adding inorganic salt, a cocatalyst, organic alkali and a phase transfer catalyst to form a raw material system, controlling to form a proper temperature, dissolving bis(trichloromethyl)carbonate in a certain amount of the organic solvent to obtain a mixture, slowly dropwise adding the mixture into the raw material system for reaction, and after the reaction is finished, carrying out column chromatography isolation, so as to obtain 2-chloroquinoline. The preparation method is simple, the reaction period is short, and a phosphorus-containing reagent and heavy metals are not adopted;and compared with the prior art, the method has the advantages that the environmental pollution is low, the operation is safe, and the cost is low. The method is applied to the environment-friendly chlorination reaction of quinoline N-oxide and is not limited to the preparation of 2-chloroquinoline.

C-Bridged Bispyrrolidines and Bispiperidines as New Ligands

The preparation of methylene-bridged C2-symmetric nitrogen-heterocycles as a new class of ligands is described, including methylene-bridged pyridines, quinolones, piperidines and pyrrolidines. These methylene-bridged aromatic systems are obtained via a microwave assisted Ziegler-type reaction. The separation of diastereomers and the application of the copper complexes of these ligands for cyclopropanation reactions proves the applicability of these new types of ligands.

Synthesis and anticancer activity evaluation of some new derivatives of 2-(4-benzoyl-1-piperazinyl)-quinoline and 2-(4-cinnamoyl-1-piperazinyl)-quinoline

In this study, we designed and synthesized twenty new derivatives of 2-(4-benzoyl-1-piperazinyl)- quinoline and 2-(4-cinnamoyl-1-piperazinyl)-quinoline with potential anticancer activity. The structures of synthesized compounds were confirmed by 1H and 13C NMR spectroscopy and MS spectrometry. The activity of novel compounds was evaluated in the cell viability assay as well as in the wound healing assay. Presented data show that examined substances have anticancer activity in cell culture. Seven compounds which showed a high rate of cell growth inhibition were selected for further studies. Three of them strongly reduced the growth of B16F10 cells. The novel compounds constitute a good base for further studies and optimization of structure for new therapeutically effective anti-cancerous drugs.

Preparation method of non-transition metal-catalyzed 2-halogenated pyridine compound

The invention provides a preparation method of a non-transition metal-catalyzed 2-halogenated pyridine compound. The 2-halogenated pyridine compound is an important component of many medicines and bioactive molecules and has important application in the fields of organic synthesis, medicinal chemistry and the like and wide market prospects. The invention relates to the preparation method of the non-transition metal-catalyzed 2-halogenated pyridine compound. According to the method, pyridine-2-carboxylic acid, derivatives of the pyridine-2-carboxylic acid, NaF, KF, CsF, TBAF, NaCl, KCl, CsCl, TBAC, NCS, NaBr, KBr, CsBr, Br2, TBAB, NBS, NaI, KI, CsI, I2 and NIS are used as raw materials, and under the presence of base and an accelerant and mild conditions, the 2-halogenated pyridine compoundis synthesized. The method has the advantages that the steps are simple, the raw materials are easy to obtain, the reaction conditions are mild and the like; the method has great use value and socialand economic benefits.

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.

Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides

This report describes a method for Pd-catalyzed decarbonylative cross-coupling that enables the conversion of carboxylic acid derivatives to biaryls, aryl amines, aryl ethers, aryl sulfides, aryl boronate esters, and trifluoromethylated arenes. The success of this transformation leverages the Pd0/Brettphos-catalyzed decarbonylative chlorination of aroyl chlorides, which can then participate in diverse cross-coupling reactions in situ using the same Pd catalyst.

N, N-disubstituted benzo-nitrogen heterocycles-2-amine compound and use thereof

The invention mainly relates to an N,N-double substituted benzoazacyclo-2-amide compound and an application thereof. The N,N-double substituted benzoazacyclo-2-amide compound is a compound shown as formula I or a salt formed by a medical acid or alkali. The compound provided by the invention has strong inhibition activity on RhoA protease which is tightly related with cardiovascular and cerebrovascular diseases. The compound provided by the invention is hopeful to be developed into a RhoA protease small-molecule inhibitor type cardiovascular and cerebrovascular disease treatment medicine.

Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh3/Cl3CCN

A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.