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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/04/07 23:28:00」(JST)

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Not to be confused with quinolone.

Quinoline is a heterocyclic aromatic organic compound with the chemical formula C₉H₇N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. A prominent example is quinine, which is found naturally in plants as alkaloids. 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance.

Occurrence and isolation

Quinoline was first extracted from coal tar in 1834 by Friedlieb Ferdinand Runge.^[3] Coal tar remains the principal source of commercial quinoline.^[4]

Like other nitrogen heterocyclic compounds, such as pyridine derivatives, quinoline is often reported as an environmental contaminant associated with facilities processing oil shale or coal, and has also been found at legacy wood treatment sites. Owing to high water solubility quinoline has significant potential for mobility in the environment, which may promote water contamination. Quinoline is readily degradable by certain microorganisms, such as Rhodococcus species Strain Q1, which was isolated from soil and paper mill sludge.^[5]

Quinoline is present in small amounts in crude oil within the virgin diesel fraction. It can be removed by hydrotreating often with a nickel-molybdenum on alumina catalyst.

Synthesis

Quinolines can be synthesized from simple anilines using a number of named reactions.

Going clockwise from top these are:

Combes quinoline synthesis using anilines and β-diketones.
Conrad-Limpach synthesis using anilines and β-ketoesters.
Doebner reaction using anilines with an aldehyde and pyruvic acid to form quinoline-4-carboxylic acids
Doebner-Miller reaction using anilines and α,β-unsaturated carbonyl compounds.
Gould-Jacobs reaction starting from an aniline and ethyl ethoxymethylenemalonate
Skraup synthesis using ferrous sulfate, glycerol, aniline, nitrobenzene, and sulfuric acid.

A number of other processes exist, which require specifically substituted anilines or related compounds:

Camps quinoline synthesis utilizing an o-acylaminoacetophenone and hydroxide
Friedländer synthesis using 2-aminobenzaldehyde and acetaldehyde.
Knorr quinoline synthesis, using a β-ketoanilide and sulfuric acid.
Niementowski quinoline synthesis, using anthranilic acid and ketones.
Pfitzinger reaction using an isatin with base and a carbonyl compound to yield substituted quinoline-4-carboxylic acids
Povarov reaction using an aniline, a benzaldehyde and an activated alkene.

Applications

Quinoline is used in the manufacture of dyes, the preparation of hydroxyquinoline sulfate and niacin. It has also used as a solvent for resins and terpenes.

Quinoline is mainly used as a feedstock in the production of other specialty chemicals. Approximately 4 tonnes are produced annually according to a report published in 2005.^[4] Its principal use is as a precursor to 8-hydroxyquinoline, which is a versatile chelating agent and precursor to pesticides. Its 2- and 4-methyl derivatives are precursors to cyanine dyes. Oxidation of quinoline affords quinolinic acid (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide sold under the name "Assert".^[4]

References

^ "QUINOLINE (BENZOPYRIDINE)". Chemicalland21.com. Retrieved 2012-06-14.
^ Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., Determination of Organic Structures by Physical Methods, Academic Press, New York, 1955.
^ "Quinoline". Encyclopædia Britannica. 1911.
^ ^a ^b ^c Gerd Collin; Hartmut Höke (2005), "Quinoline and Isoquinoline", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a22_465
^ O'Loughlin, Edward J.; Kehrmeyer, Staci R.; Sims, Gerald K. (1996). "Isolation, characterization, and substrate utilization of a quinoline-degrading bacterium". International Biodeterioration & Biodegradation 38 (2): 107. doi:10.1016/S0964-8305(96)00032-7.

External links

International Chemical Safety Card 0071
New methods of synthesizing quinolines

UpToDate Contents

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1. 抗マラリア剤：概要 antimalarial drugs an overview

English Journal

Sensitive and rapid determination of quinoline yellow in drinks using polyvinylpyrrolidone-modified electrode.

Zhang S1, Shi Z2, Wang J2.
Food chemistry.Food Chem.2015 Apr 15;173:449-53. doi: 10.1016/j.foodchem.2014.10.050. Epub 2014 Oct 18.
A novel electrochemical sensor using polyvinylpyrrolidone (PVP)-modified carbon paste electrode was developed for the sensitive and rapid determination of quinoline yellow. In 0.1M, pH 6.5 phosphate buffer, an irreversible oxidation wave at 0.97 V was observed for quinoline yellow. PVP exhibited str
PMID 25466044

Synthesis and structure of interaction products of quinoline-2(1H)-thione with molecular iodine.

Chernov'yants MS1, Starikova ZA2, Kolesnikova TS3, Karginova AO3, Lyanguzov NV4.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2015 Mar 15;139:533-8. doi: 10.1016/j.saa.2014.12.075. Epub 2014 Dec 27.
The behavior of quinoline-2(1H)-thione, which is a potential antithyroid drug toward molecular iodine, was investigated. The ability of quinoline-2(1H)-thione to form the outer-sphere charge-transfer complex C9H7NS·I2 with iodine molecular in dilute chloroform solution has been studied by UV-vis sp
PMID 25579655

Novel carbazole derivatives with quinoline ring: Synthesis, electronic transition, and two-photon absorption three-dimensional optical data storage.

Li L1, Wang P2, Hu Y3, Lin G1, Wu Y4, Huang W3, Zhao Q1.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2015 Mar 15;139:243-52. doi: 10.1016/j.saa.2014.10.122. Epub 2014 Dec 24.
We designed carbazole unit with an extended π conjugation by employing Vilsmeier formylation reaction and Knoevenagel condensation to facilitate the functional groups of quinoline from 3- or 3,6-position of carbazole. Two compounds doped with poly(methyl methacrylate) (PMMA) films were prepared. To
PMID 25561303

Japanese Journal

Preparation and reaction of quinolinyl (or pyridinyl)phosphonium salts with base and pivalaldehyde

Shimada Minami,Sugimoto Osamu,Sato Akihiro [他]
Heterocycles 83(4), 837-847, 2011-04-01
NAID 40018733656

Reversible dehydrogenation-hydrogenation of tetrahydroquinoline-quinoline using a supported copper nanoparticle catalyst

Mikami Yusuke,Ebata Kaori,Mitsudome Takato [他]
Heterocycles 82(2), 1371-1377, 2011-03-01
NAID 40018702725

Related Pictures

★リンクテーブル★

リンク元	「駆虫薬」
拡張検索	「4-hydroxyaminoquinoline-1-oxide」「pyrrolo-quinoline quinone」

「駆虫薬」

Quinoline
	IUPAC name quinoline
	Systematic name 2-azabicyclo[4.4.0]deca-1(6),2,4,7,9-pentaene; 2-azabicyclo[4.4.0]deca-1,3,5,7,9-pentaene; benzo[b]azine; benzo[b]azabenzene;
	Other names 1-azanaphthalene; benzo[b]pyridine; 1-benzazine; benzazine; benzazabenzene; benzopyridine; 1-benzine; quinolin; chinoline; chinoleine; chinolin; leucol; leukol; leucoline;
Identifiers
CAS number	91-22-5
PubChem	7047
ChemSpider	6780
UNII	E66400VT9R
EC number	202-051-6
UN number	2656
KEGG	C06413
MeSH	Quinolines
ChEBI	CHEBI:17362
ChEMBL	CHEMBL14474
RTECS number	VA9275000
3DMet	B00959
Jmol-3D images	Image 1
	SMILES n1cccc2ccccc12 ;
	InChI InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H ; Key: SMWDFEZZVXVKRB-UHFFFAOYSA-N InChI=1/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H; Key: SMWDFEZZVXVKRB-UHFFFAOYAU ;
Properties
Molecular formula	C9H7N
Molar mass	129.16 g/mol
Appearance	yellowish oily liquid
Density	1.093 g/mL
Melting point	−15 °C
Boiling point	237 °C/760 mm Hg, 108-110 °C/11 mm Hg
Solubility in water	Slightly soluble
Solubility	Soluble in alcohol, ether, and carbon disulfide
Acidity (pKa)	4.85
Thermochemistry
Std enthalpy of; formation ΔfHo298	174.9 kJ mol−1
Hazards
R-phrases	R21, R22
S-phrases	S26, S27, S28, S29, S30, Template:S31, Template:S32, S33, Template:S34, S35, S36
NFPA 704	1 2 0
Flash point	101 °C (214 °F; 374 K)
LD50	331 mg/kg
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
	(verify) (what is: /?)
	Infobox references

　　[★]

英: anthelmintic, anthelmintics
ラ: anthelmintica
関

http://en.wikipedia.org/wiki/Anthelmintic

antiplatyhelmintic agents	Antitrematodals (schistosomicides)	binds tubulin	benzimidazole (Triclabendazole#)
		acetylcholinesterase inhibitor	phosphonic acid (metrifonate)
		Other/unknown	quinoline (praziquantel#, oxamniquine#) · phenol (bithionol) · thiazole ([[niridazole]) · arylsulfonate (stibophen)
	anticestodals (taeniacides)	binds tubulin	benzimidazole (albendazole#)
	anticestodals (taeniacides)	Other/unknown	salicylanilide (niclosamide)# · aminoacridine (quinacrine) · butyrophenone (desaspidin) · chlorophenol (dichlorophen)
antinematodal agents (macrofilaricides)		binds tubulin	benzimidazole (mebendazole#, thiabendazole, albendazole#, fenbendazole, ciclobendazole, flubendazole)
		chloride channel	macrolide (ivermectin#)
		NMDA	tetrahydropyrimidine (pyrantel#, pyrantel pamoate, oxantel)
		Other/unknown	piperazine (piperazine · diethylcarbamazine#) · thiazole (levamisole#) · quinolinium (pyrvinium) · benzylammonium (bephenium) · naphthalenesulfonate (suramin#) · tribendimidine

「4-hydroxyaminoquinoline-1-oxide」

　　[★]

4-ヒドロキシアミノキノリン-1-オキシド

「pyrrolo-quinoline quinone」

　　[★] ピロロキノリンキノン

[1] "QUINOLINE (BENZOPYRIDINE)". Chemicalland21.com. Retrieved 2012-06-14.

[2] Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., Determination of Organic Structures by Physical Methods, Academic Press, New York, 1955.

[3] "Quinoline". Encyclopædia Britannica. 1911.

[Hoke-4] Gerd Collin; Hartmut Höke (2005), "Quinoline and Isoquinoline", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a22_465

[5] O'Loughlin, Edward J.; Kehrmeyer, Staci R.; Sims, Gerald K. (1996). "Isolation, characterization, and substrate utilization of a quinoline-degrading bacterium". International Biodeterioration & Biodegradation 38 (2): 107. doi:10.1016/S0964-8305(96)00032-7.

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案内

quinoline