Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Quinoline: Difference between pages

{{distinguish|quinolone}}

{{see also|Quinoline Yellow (disambiguation){{!}}Quinoline Yellow}}

{{Chembox

|Watchedfields = changed

|verifiedrevid = 464378790

|ImageFile = Quinoline chemical structure.svg

|ImageSize = 250px

|ImageFileL1 = Quinoline-3D-balls-2.png

|ImageSizeL1 = 120

|ImageAltL1 = Quinoline molecule

|ImageNameL1 = C=black, H=white, N=blue

|ImageFileR1 = Quinoline-3D-spacefill.png

|ImageSizeR1 = 120

|ImageNameR1 = C=black, H=white, N=blue

|ImageAltR1 = Quinoline molecule

|PIN = Quinoline<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | pages = 4, 211 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = The name ‘quinoline’ is a retained name that is preferred to the alternative systematic fusion names ‘1-benzopyridine’ or ‘benzo[''b'']pyridine’.}}</ref>

|SystematicName = {{unbulleted list|1-Benzopyridine<!-- P-25.2.2.4 -->|Benzo[''b'']pyridine<!-- P-25.3.1.3 -->|<!-- von Baeyer Nomenclature -->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|<!-- Fused Ring Nomenclature -->Benzo[''b'']azine|Benzo[''b'']azabenzene}}

|OtherNames = {{unbulleted list|1-Azanaphthalene|1-Benzazine<!-- not recommended according to 2013 IUPAC recommendations -->|Benzazine|Benzazabenzene|Benzopyridine|1-Benzine|Quinolin|Chinoline|Chinoleine|Chinolin|Leucol|Leukol|Leucoline}}

|Section1 = {{Chembox Identifiers

|CASNo = 91-22-5

|CASNo_Ref = {{cascite|correct|CAS}}

|Beilstein = 107477

|PubChem = 7047

|ChemSpiderID = 6780

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|EINECS = 202-051-6

|Gmelin = 27201

|UNNumber = 2656

|KEGG = C06413

|KEGG_Ref = {{keggcite|correct|kegg}}

|MeSHName = Quinolines

|ChEBI = 17362

|ChEBI_Ref = {{ebicite|correct|EBI}}

|ChEMBL = 14474

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|RTECS = VA9275000

|SMILES = n1cccc2ccccc12

|SMILES1 = C1=CC=C2C(=C1)C=CC=N2

|StdInChI = 1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = SMWDFEZZVXVKRB-UHFFFAOYSA-N

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|InChI = 1/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H

|InChIKey = SMWDFEZZVXVKRB-UHFFFAOYAU

|UNII = E66400VT9R

|UNII_Ref = {{fdacite|correct|FDA}}

|3DMet = B00959

|Section2 = {{Chembox Properties

|Formula = C₉H₇N

|MolarMass = 129.16{{nbsp}}g/mol

|Appearance = Colorless oily liquid

|Density = 1.093{{nbsp}}g/mL

|MeltingPtC = −15

|BoilingPtC = 237

|BoilingPt_notes =, 760{{nbsp}}mm{{nnbsp}}Hg; {{convert|108|–|110|°C}}, 11{{nbsp}}mm{{nnbsp}}Hg

|Solubility = Slightly soluble

|pKa = 4.85 (conjugated acid)<ref>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.</ref>

|SolubleOther = Soluble in alcohol, ether, and carbon disulfide

|MagSus = −86.0·10⁻⁶{{nbsp}}cm³/mol

|Section3 = {{ Chembox Thermochemistry

|DeltaHf = 174.9{{nbsp}}kJ·mol⁻¹

|Section4 = {{Chembox Hazards

|NFPA-H = 2

|NFPA-F = 1

|NFPA-R = 0

|GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}}

|GHSSignalWord = Danger

|HPhrases = {{H-phrases|302|312|315|319|341|350|411}}

|PPhrases = {{P-phrases|201|202|264|270|273|280|281|301+312|302+352|305+351+338|308+313|312|321|322|330|332+313|337+313|362|363|391|405|501}}

|FlashPtC = 101

|AutoignitionPtC = 400

|LD50 = 331{{nbsp}}mg/kg

}}

| Reference = <ref>{{cite web |url=http://www.chemicalland21.com/industrialchem/organic/QUINOLINE.htm |title=QUINOLINE (BENZOPYRIDINE) |work=Chemicalland21.com |access-date=2012-06-14}}</ref>

}}

'''Quinoline''' is a [[heterocyclic]] [[aromatic]] [[organic compound]] with the chemical formula C₉H₇N. It is a colorless [[hygroscopic]] liquid with a strong odor. Aged samples, especially 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.<ref name=EB1911>{{cite EB1911 |wstitle=Quinoline |volume=22 |page=759}}</ref> Quinoline itself has few applications, but many of its [[derivative (chemistry)|derivatives]] are useful in diverse applications. A prominent example is [[quinine]], an [[alkaloid]] found in plants. Over 200 biologically active quinoline and [[quinazoline]] alkaloids are identified.<ref>{{cite journal |last1=Shang |first1=XF |last2=Morris-Natschke |first2=SL |last3=Liu |first3=YQ |last4=Guo |first4=X |last5=Xu |first5=XS |last6=Goto |first6=M |last7=Li |first7=JC |last8=Yang |first8=GZ |last9=Lee |first9=KH |title=Biologically active quinoline and quinazoline alkaloids part I. |journal=Medicinal Research Reviews |date=May 2018 |volume=38 |issue=3 |pages=775–828 |doi=10.1002/med.21466 |pmid=28902434 |pmc=6421866 }}</ref><ref>{{cite journal |last1=Shang |first1=Xiao-Fei |last2=Morris-Natschke |first2=Susan L. |last3=Yang |first3=Guan-Zhou |last4=Liu |first4=Ying-Qian |last5=Guo |first5=Xiao |last6=Xu |first6=Xiao-Shan |last7=Goto |first7=Masuo |last8=Li |first8=Jun-Cai |last9=Zhang |first9=Ji-Yu |last10=Lee |first10=Kuo-Hsiung |title=Biologically active quinoline and quinazoline alkaloids part II |journal=Medicinal Research Reviews |date=September 2018 |volume=38 |issue=5 |pages=1614–1660 |doi=10.1002/med.21492 |pmid=29485730 |pmc=6105521 }}</ref> [[4-Hydroxy-2-alkylquinoline]]s (HAQs) are involved in [[antibiotic resistance]].

== Occurrence and isolation ==

Quinoline was first extracted from [[coal tar]] in 1834 by German chemist [[Friedlieb Ferdinand Runge]];<ref name=EB1911/> he called quinoline ''leukol'' ("white oil" in Greek).<ref>F. F. Runge (1834) [https://books.google.com/books?id=wCUAAAAAMAAJ&pg=PA65 "Ueber einige Produkte der Steinkohlendestillation"] (On some products of coal distillation), ''Annalen der Physik und Chemie'', '''31''' (5) : 65–78; see especially p. 68: "3. Leukol oder Weissöl" (3. White oil [in Greek] or white oil [in German]). From p. 68: ''"Diese dritte Basis habe ich Leukol oder Weissöl genannt, weil sie keine farbigen Reactionen zeigt."'' (This third base I've named ''leukol'' or white oil because it shows no color reactions.)</ref> Coal tar remains the principal source of commercial quinoline.<ref name=Hoke/> In 1842, French chemist [[Charles Frédéric Gerhardt|Charles Gerhardt]] obtained a compound by dry distilling [[quinine]], [[strychnine]], or [[cinchonine]] with [[potassium hydroxide]];<ref name=EB1911/> he called the compound ''Chinoilin'' or ''Chinolein''.<ref>Gerhardt, Ch. (1842) [https://babel.hathitrust.org/cgi/pt?id=mdp.39015026322233;view=1up;seq=710 "Untersuchungen über die organischen Basen"] (Investigations of organic bases), ''Annalen der Chemie und Pharmacie'', '''42''' : 310-313. See also: (Editor) (1842) [https://babel.hathitrust.org/cgi/pt?id=hvd.hx3bgp;view=1up;seq=675 "Chinolein oder Chinoilin"] (Quinoline or quinoilin), ''Annalen der Chemie und Pharmacie'', '''44''' : 279-280.</ref> Runge's and Gephardt's compounds seemed to be distinct [[isomers]] because they reacted differently. However, the German chemist [[August Wilhelm von Hofmann|August Hoffmann]] eventually recognized that the differences in behaviors was due to the presence of contaminants and that the two compounds were actually identical.<ref>Initially, Hoffmann thought that Runge's ''Leukol'' and Gerhardt's ''Chinolein'' were distinct. (See: Hoffmann, August Wilhelm (1843) [https://babel.hathitrust.org/cgi/pt?id=hvd.hx3bgr;view=1up;seq=51 "Chemische Untersuchungen der organischen Basen im Steinkohlen-Theeröl"] (Chemical investigations of organic bases in coal tar oil), ''Annalen der Chemie und Pharmacie'', '''47''' : 37-87; see especially pp. 76-78.) However, after further purification of his ''Leukol'' sample, Hoffmann determined that the two were indeed identical. (See: (Editor) (1845) [https://babel.hathitrust.org/cgi/pt?id=uiug.30112025846970;view=1up;seq=442 "Vorläufige Notiz über die Identität des Leukols und Chinolins"] (Preliminary notice of the identity of leukol and quinoline), ''Annalen der Chemie und Pharmacie'', '''53''' : 427-428.)</ref> The only report of quinoline as a natural product is from the Peruvian stick insect

''Oreophoetes peruana''. They have a pair of thoracic glands from which they discharge a malodorous fluid containing quinoline when disturbed.<ref>Eisner, T; Morgan, R.C.; Attygalle A.B., Smedley, S.R.; Herath, K.B., Meinwald, J. (1997) “Defensive Production of quinoline by a phasmid insect (Oreophoetes peruana) J. Exp. Biol. 200, 2493–2500.</ref>

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 its relatively high solubility in water 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.<ref>{{cite journal | doi = 10.1016/S0964-8305(96)00032-7 | title = Isolation, characterization, and substrate utilization of a quinoline-degrading bacterium | year = 1996 | last1 = O'Loughlin | first1 = Edward J. | last2 = Kehrmeyer | first2 = Staci R. | last3 = Sims | first3 = Gerald K. | journal = International Biodeterioration & Biodegradation | volume = 38 | issue = 2 | pages = 107| bibcode = 1996IBiBi..38..107O }}</ref>

Quinolines are present in small amounts in crude oil within the virgin [[diesel fuel|diesel]] fraction. It can be removed by the process called [[hydrodenitrification]].

== Synthesis ==

Quinolines are often synthesized from simple anilines using a number of [[name reaction|named reactions]].

::[[File:Quinoline from aniline.png|400px]]

Going clockwise from top these are:

* [[Combes quinoline synthesis]] using [[aniline]]s and β-di[[ketone]]s.

* [[Conrad-Limpach synthesis]] using [[aniline]]s and β-ketoesters.

* [[Doebner reaction]] using [[aniline]]s with an [[aldehyde]] and [[pyruvic acid]] to form quinoline-4-carboxylic acids

* [[Doebner-Miller reaction]] using [[aniline]]s 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]] using an o-acylaminoacetophenone and hydroxide

* [[Friedländer synthesis]] using [[2-Aminobenzaldehyde|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]]

Quinolines are reduced to [[tetrahydroquinoline]]s enantioselectively using several catalyst systems.<ref>Xu, L.; Lam, K. H.; Ji, J.; Wu, J.; Fan, Q.-H.; Lo, W.-H.; Chan, A. S. C. ''Chem. Commun.'' '''2005''', 1390.</ref><ref>Reetz, M. T.; Li, X. ''Chem. Commun.'' '''2006''', 2159.</ref>

[[File:ImineScope8.png|center]]

== Applications ==

Quinolines are used in the manufacture of [[dye]]s and the preparation of [[hydroxyquinoline]] sulfate and [[niacin (substance)|niacin]]. It is also used as a solvent for [[resin]]s and [[terpene]]s.

Quinoline is mainly used as in the production of other [[specialty chemicals]]. Approximately 4 [[tonne]]s were produced annually according to a report published in 2005.<ref name=Hoke/> Its principal use is as a precursor to [[8-hydroxyquinoline]], which is a versatile chelating agent and precursor to pesticides. Its [[quinaldine|2-]] and [[lepidine|4-methyl]] derivatives are precursors to [[cyanine dye]]s. Oxidation of quinoline affords [[quinolinic acid]] (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide sold under the name "Assert".<ref name=Hoke>{{Ullmann | author1 = Gerd Collin | author2 = Hartmut Höke | title = Quinoline and Isoquinoline | doi = 10.1002/14356007.a22_465}}</ref>

The reduction of quinoline with [[sodium borohydride]] in the presence of [[acetic acid]] is known to produce [[Kairoline A]].<ref name="GRIBBLEHEALD1975">{{cite journal|last1=GRIBBLE|first1=Gordon W.|last2=HEALD|first2=Peter W.|title=Reactions of Sodium Borohydride in Acidic Media; III. Reduction and Alkylation of Quinoline and Isoquinoline with Carboxylic Acids|journal=Synthesis|volume=1975|issue=10|year=1975|pages=650–652|issn=0039-7881|doi=10.1055/s-1975-23871}}</ref> (C.f. [[Kairine]])

Several [[Antimalarial medication|anti-malarial]] drugs contain quinoline substituents. These include [[Antimalarial medication#Quinine and related agents|quinine]], [[Antimalarial medication#Chloroquine|chloroquine]], [[Antimalarial medication#Amodiaquine|amodiaquine]], and [[Antimalarial medication#Primaquine|primaquine]].

Quinoline is used as a solvent and reagent in organic synthesis.<ref>{{cite book |doi=10.1002/047084289X.rq002.pub2 |chapter=Quinoline |title=Encyclopedia of Reagents for Organic Synthesis |year=2001 |last1=Sherman |first1=Angela R. |last2=Caron |first2=Antoine |last3=Collins |first3=Shawn K. |pages=1–4 |isbn=9780470842898 }}</ref>

Quinolinium compounds (e.g. salts) can also be used as corrosion inhibitors and intensifiers.

== See also ==

* [[Quinoline alkaloids]]

* [[4-Aminoquinoline]]

* [[8-Hydroxyquinoline]]

* [[Pyrroloquinoline quinone]] (PQQ), a redox cofactor and controversial nutritional supplement

* [[Quinazoline]], an aza derivative of quinoline

* [[Quinine]]

* Similar [[simple aromatic ring]]s

** [[Isoquinoline]], an analog with the nitrogen atom in position 2

** [[Pyridine]], an analog without the fused [[benzene]] ring

** [[Naphthalene]], an analog with a carbon instead of the nitrogen

** [[Indole]], an analog with only a five-membered nitrogen ring

==References==

{{Reflist}}

==External links==

{{Commons category}}

*{{ICSC|0071|00}}

*[https://www.organic-chemistry.org/synthesis/heterocycles/benzo-fused/quinolines.shtm New methods of synthesizing quinolines]

{{Authority control}}

[[Category:Quinolines| ]]

[[Category:Amine solvents]]

[[Category:Simple aromatic rings]]

[[Category:Foul-smelling chemicals]]

[[Category:Substances discovered in the 19th century]]