Reissert reaction

The Reissert reaction is a series of chemical reactions that transforms quinoline to quinaldic acid.^[1][2] 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.

The Reissert reaction

The Reissert reaction is also successful with isoquinolines^[3][4] and most pyridines.

Several reviews have been published.^[5][6]

References

1. ^ Reissert, Arnold (1905). "Ueber die Einführung der Benzoyl-gruppe in tertiäre cyclische Basen". Berichte der deutschen chemischen Gesellschaft. 38 (2): 1603–1614. doi:10.1002/cber.19050380260.
2. ^ Grosheintz, J. M.; Fischer, Hermann O. L. (1941). Journal of the American Chemical Society. 63 (7): 2021–2022. doi:10.1021/ja01852a066. {{cite journal}}: Missing or empty |title= (help)
3. ^ Weinstock, J.; Boekelheide, V. Organic Syntheses, Coll. Vol. 4, p. 641 (1963); Vol. 38, p. 58 (1958). (Article)
4. ^ Uff, B. C.; Kershaw, J. R.; Neumeyer, J. L. Organic Syntheses, Coll. Vol. 6, p. 115 (1988); Vol. 56, p. 19 (1977). (Article)
5. ^ Mosettig, E. Org. React. 1954, 8, 220. (Review)
6. ^ McEwen, William E.; Cobb, R. Lynn (1955). "The Chemistry of N-Acyldihydroquinaldonitriles and N-Acyldihydroisoquinaldonitriles (Reissert Compounds)". Chemical Reviews. 55 (3): 511–549. doi:10.1021/cr50003a002. (Review)
7. ^ Ahamed, Muneer; Todd, Matthew. H. (2010). "Catalytic Asymmetric Additions of Carbon-Centered Nucleophiles to Nitrogen-Containing Aromatic Heterocycles". European Journal of Organic Chemistry. 2010 (31): 5935–5942. doi:10.1002/ejoc.201000877. (Review)

Further reading

1. Cobb, R. Lynn; McEwen, William E. (1955). Journal of the American Chemical Society. 77 (19): 5042. doi:10.1021/ja01624a031. {{cite journal}}: Missing or empty |title= (help)
2. McEwen, William E.; Mineo, Isidore C.; Shen, Yvonne H. (1971). "1,3-Dipolar addition reactions of Reissert compounds". Journal of the American Chemical Society. 93 (18): 4479. doi:10.1021/ja00747a023.
3. Evanguelidou, Eleftheria K.; McEwen, William E. (1966). "Acid-Catalyzed Condensation of a Reissert Compound with Acrylonitrile". The Journal of Organic Chemistry. 31 (12): 4110. doi:10.1021/jo01350a056.