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

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

References

1. ^ Reissert, A. Ber. 1905, 38, 1603.
2. ^ Grosheintz, J. M.; Fischer, H. O. L. J. Am. Chem. Soc. 1941, 63, 2021.
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, W. E.; Cobb, R. L. Chem. Rev. 1955, 55, 511. (Review)
7. ^ Ahamed, M.; Todd, M. H. " Eur. J. Org. Chem." 2010, 31, 5935. (Article) (Review)