Hydrochloric Acid → 4-[(3-Butyl-4-quinolinyl)-methyl]-benzonitrile

Participants

Reaction Conditions

Reaction Steps

14 ml of a 0.38M solution of 4-bromomethyl benzonitrile zinc in tetrahydrofuran (prepared by Knochel, J. Org. Chem., (1988) Vol. 53, pages 5789 to 5791) were added to a stirred mixture of 0.720 g of 4-chloro-3-butyl quinoline of Step F with 0.8 ml of tetrahydrofuran and 0.663 g of tetrakis triphenylphosphine palladium. The mixture was stirred for 4 hours at 60° C., then for 16 hours at ambient temperature. The mixture was hydrolyzed with 100 ml of 0.1N hydrochloric acid and then extracted with ethyl acetate. The extracts were washed with a saturated solution of sodium chloride, dried and evaporated to dryness. The residue was chromatographed on silica (eluant: hexane--ethyl acetate (7-3)) to obtain 0.445 g of the desired product.

Provenance & Evidence