Tetrahydroquinoline is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

that is the semi-hydrogenated derivative of

quinoline 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 sli ...

. It is a colorless oil.

Use

Substituted derivatives of tetrahydroquinoline are common in

medicinal chemistry Medicinal or pharmaceutical chemistry is a scientific discipline at the intersection of chemistry and pharmacy involved with designing and developing pharmaceutical drugs. Medicinal chemistry involves the identification, synthesis and developme ...

Oxamniquine Oxamniquine, sold under the brand name Vansil among others, is a medication used to treat schistosomiasis due to ''Schistosoma mansoni''. Praziquantel, however, is often the preferred treatment. It is given by mouth and used as a single dose. Co ...

, dynemycin, viratmycin, and nicainoprol are bioactive tetrahydroquinolines. Typically tetrahydroquinoline derivatives are prepared by

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic ...

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 A hydrogen-donor solvent is hydrocarbon that transfers hydrogen to hydrogen-poor substrates, such as coal. The hydrogen-poor substrates could be a solute or suspension. The classic hydrogen-donor solvent (or just donor solvent) is tetrahydronapht ...

in coal liquifaction. Using homogeneous catalysts, asymmetric hydrogenation has been demonstrated. It can also be prepared from

1-indanone 1-Indanone is the organic compound with the formula C6H4(CH2)2CO. It is one of two isomeric benzocyclopentanones, the other being 2-indanone. It is a colorless solid. 1-Indanone is a substrate for the enzyme indanol dehydrogenase. Preparation ...

(benzocyclopentanone).

References

{{reflist Amine solvents