Aniline → 4'-[(2-Ethylquinolin-4-yloxy)methyl]biphenyl-2-carbonitrile

Participants

Reaction Steps

A mixture of 2-ethyl-4-quinolone (1.73 g), (prepared by a similar method to that described in Org. Syn., Coll. Vol. III, p.374 and p.593 from aniline and methyl propionylacetate), 4'-bromomethylbiphenyl-2-carbonitrile (A) (3.1 g) and solid potassium carbonate (1.81 g) in N-methylpyrrolidone (40 ml) were stirred for 36 hours under nitrogen. The mixture was then added dropwise to water (100 ml) at 15°-25° C. and stirred for 30 minutes. The suspended solid was collected by filtration, washed with water, and dried at 60° C. under vacuum. The solid was recrystallised from tert-butyl methyl ether to give 4'-[(2-ethylquinolin-4-yloxy)methyl]-biphenyl-2-carbonitrile as a solid (1.9 g), m.p. 151°-153° C.; NMR(CDCl3): 1.4(t, 3H), 2.97(q,2H), 5.35(s,2H), 6.76(s,1H), 7.4-7.6(m, 3H), 7.6-7.8(m, 6H), 8.0(d, 1H), 8.25(d, 1H).

Provenance & Evidence