Reissert reaction

{{Reactionbox

| Name = Reissert reaction

| Type = Addition reaction

| NamedAfter = Arnold Reissert

}}

The Reissert reaction is a series of chemical reactions that transforms quinoline to quinaldic acid.{{Ref|Reissert1905}}{{Ref|Gronsheintz1941}} Quinolines will react with acid chlorides and potassium cyanide to give 1-acyl-2-cyano-1,2-dihydroquinolines, also known as Reissert compounds. Hydrolysis gives the desired quinaldic acid.

Image:Reissert Reaction Scheme.png

The Reissert reaction is also successful with isoquinolines{{Ref|Weinstock1958}}{{Ref|Uff1977}} and most pyridines.

Several reviews have been published.{{Ref|Mosettig1954}}{{Ref|McEwen1955}}

References

{{Note|Reissert1905}} {{cite journal | doi =10.1002/cber.19050380260 | pages= 1603–1614 | title =Ueber die Einführung der Benzoyl-gruppe in tertiäre cyclische Basen | year =1905 | last1 =Reissert | first1 =Arnold | journal= Berichte der deutschen chemischen Gesellschaft | volume =38 | issue =2| url= https://zenodo.org/record/1426154 }}
{{Note|Grosheintz1941}} {{cite journal | doi =10.1021/ja01852a066 | pages=2021–2022 | year =1941 | last1 =Grosheintz | first1 =J. M. | last2 =Fischer | first2 =Hermann O. L. | title=Preparation of 1-Acyl-1,2-dihydroquinaldonitriles and their Hydrolysis to Aldehydes | journal =Journal of the American Chemical Society | volume =63 | issue =7}}
{{Note|Weinstock1958}} Weinstock, J.; Boekelheide, V. Organic Syntheses, Coll. Vol. 4, p. 641 (1963); Vol. 38, p. 58 (1958). ([http://www.orgsyn.org/orgsyn/prep.asp?prep=cv4p0641 Article])
{{Note|Uff1977}} Uff, B. C.; Kershaw, J. R.; Neumeyer, J. L. Organic Syntheses, Coll. Vol. 6, p. 115 (1988); Vol. 56, p. 19 (1977). ([http://www.orgsyn.org/orgsyn/prep.asp?prep=cv6p0115 Article])
{{Note|Mosettig1954}} Mosettig, E. Org. React. 1954, 8, 220. (Review)
{{Note|McEwen1955}} {{cite journal | doi = 10.1021/cr50003a002 | pages = 511–549 | title = The Chemistry of N-Acyldihydroquinaldonitriles and N-Acyldihydroisoquinaldonitriles (Reissert Compounds) | year = 1955 | last1 = McEwen | first1 = William E. | last2 = Cobb | first2 = R. Lynn | journal = Chemical Reviews | volume = 55 | issue = 3| hdl = 1808/32921 | hdl-access = free }} (Review)
{{Note|Ahamed2010}} {{cite journal | doi = 10.1002/ejoc.201000877 | pages = 5935–5942 | title = Catalytic Asymmetric Additions of Carbon-Centered Nucleophiles to Nitrogen-Containing Aromatic Heterocycles | year = 2010 | last1 = Ahamed | first1 = Muneer | last2 = Todd | first2 = Matthew. H. | journal = European Journal of Organic Chemistry | volume = 2010 | issue = 31}} (Review)

Reissert reaction

References

Further reading