Tetrahydroquinoline

Tetrahydroquinoline
Names
	IUPAC name 1,2,3,4-Tetrahydroquinoline
	Other names Hydroquinoline
Identifiers
CAS Number	635-46-1;
3D model (JSmol)	Interactive image;
Beilstein Reference	116149
ChEBI	CHEBI:213323;
ChEMBL	ChEMBL303611;
ChemSpider	62667;
ECHA InfoCard	100.010.216
EC Number	211-237-6;
Gmelin Reference	27202
PubChem CID	69460;
UNII	CCR50N1Z9G;
CompTox Dashboard (EPA)	DTXSID8060903 ;
	InChI InChI=1S/C9H11N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-2,4,6,10H,3,5,7H2 Key: LBUJPTNKIBCYBY-UHFFFAOYSA-N;
	SMILES C1CC2=CC=CC=C2NC1;
Properties
Chemical formula	C9H11N
Molar mass	133.194 g·mol−1
Appearance	Colorless oily liquid
Density	1.0599 g/cm3
Melting point	20 °C (68 °F; 293 K)
Boiling point	251 °C (484 °F; 524 K)
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H315, H319, H335, H350
GHS precautionary statements	P201, P202, P261, P264, P271, P280, P281, P302+352, P304+340, P305+351+338, P308+313, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
Related compounds
Related compounds	Quinoline, Tetralin, Chromane
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Tetrahydroquinoline is an organic compound that is the semi-hydrogenated derivative of quinoline. It is a colorless oil.

Use

Substituted derivatives of tetrahydroquinoline are common in medicinal chemistry.[1] Oxamniquine, dynemycin, viratmycin, and nicainoprol are bioactive tetrahydroquinolines.[2] Typically tetrahydroquinoline derivatives are prepared by hydrogenation of the corresponding quinoline using heterogeneous catalysts.

Synthesis

Tetrahydroquinolines are produced by hydrogenation of quinolines. Because the hydrogenation is reversible, tetrahydroquinoline has been often examined as a hydrogen-donor solvent in coal liquifaction.

Using homogeneous catalysts, asymmetric hydrogenation has been demonstrated.[3] It can also be prepared from 1-indanone (benzocyclopentanone).[4]

References

Sridharan, Vellaisamy; Suryavanshi, Padmakar A.; Menéndez, J. Carlos (2011). "Advances in the Chemistry of Tetrahydroquinolines". Chemical Reviews. 111 (11): 7157–7259. doi:10.1021/cr100307m. PMID 21830756.
Katritzky, Alan R.; Rachwal, Stanislaw; Rachwal, Bogumila (1996). "Recent Progress in the Synthesis of 1,2,3,4-Tetrahydroquinolines". Tetrahedron. 52 (48): 15031–15070. doi:10.1016/S0040-4020(96)00911-8.
Chen, Fei; Ding, Zi-Yuan; He, Yan-Mei; Fan, Qing-Hua (2015). "Synthesis of Optically Active 1,2,3,4-Tetrahydroquinolines via Asymmetric Hydrogenation Using Iridium-Diamine Catalyst". Organic Syntheses. 92: 213–226. doi:10.15227/orgsyn.092.0213.
Imaizumi, Taku; Okano, Kentaro; Tokuyama, Hidetoshi (2016). "DIBALH-Mediated Reductive Ring-Expansion Reaction of Cyclic Ketoxime". Organic Syntheses. 93. pp. 1–13. doi:10.1002/0471264229.os093.01. ISBN 9780471264224.

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[1] Sridharan, Vellaisamy; Suryavanshi, Padmakar A.; Menéndez, J. Carlos (2011). "Advances in the Chemistry of Tetrahydroquinolines". Chemical Reviews. 111 (11): 7157–7259. doi:10.1021/cr100307m. PMID 21830756.

[2] Katritzky, Alan R.; Rachwal, Stanislaw; Rachwal, Bogumila (1996). "Recent Progress in the Synthesis of 1,2,3,4-Tetrahydroquinolines". Tetrahedron. 52 (48): 15031–15070. doi:10.1016/S0040-4020(96)00911-8.

[3] Chen, Fei; Ding, Zi-Yuan; He, Yan-Mei; Fan, Qing-Hua (2015). "Synthesis of Optically Active 1,2,3,4-Tetrahydroquinolines via Asymmetric Hydrogenation Using Iridium-Diamine Catalyst". Organic Syntheses. 92: 213–226. doi:10.15227/orgsyn.092.0213.

[4] Imaizumi, Taku; Okano, Kentaro; Tokuyama, Hidetoshi (2016). "DIBALH-Mediated Reductive Ring-Expansion Reaction of Cyclic Ketoxime". Organic Syntheses. 93. pp. 1–13. doi:10.1002/0471264229.os093.01. ISBN 9780471264224.