Friedlaender Synthesis

P. Friedlaender, Ber. 15, 2572 (1882); P. Friedlaender, C. F. Gohring, ibid. 16, 1833 (1883).

Base-catalyzed condensation of 2-aminobenzaldehydes with ketones to form quinoline derivatives:

Reviews: R. H. Manske, Chem. Rev. 30, 124 (1942); C. C. Cheng, S. J. Yan, Org. React. 28, 37 (1982). Cyclic ketones containing S, or N: G. Kempter, S. Hirschberg, ibid. 98, 419 (1965); K. Rao et al., J. Heterocyclic Chem. 16, 1241 (1979). Modified conditions: I.-S. Cho et al., J. Org. Chem. 56, 7288 (1991); G. Sabitha et al., Synth. Commun. 29, 4403 (1999). Review: R. P. Thummel, Synlett. 1992, 1-12. Cf. Niementowski Quinoline Synthesis; Pfitzinger Reaction.