Acetic Acid → 5,6,7,8-Tetrahydro-N-phenyl-7-quinolinamine

Participants

Reaction Steps

Glacial acetic acid (1.2 ml, 20 mmol) was added dropwise to a stirred solution of 5,6-dihydroquinoline (1.31 g, 10 mmol) and aniline (1.86 g, 20 mmol) in methanol (4 ml). The solution was heated under reflux for 21h, cooled to room temperature, poured onto a mixture of saturated aqueous sodium chloride (25 ml) and water (25 ml), and the mixture was basified with 10N-NaOH and extracted with ether (3×25 ml). The extracts were concentrated in vacuo to give a dark orange oil which was chromatographed [alumina; ethyl acetate-toluene (1:24 to 1:4)] to give a solid. Recrystallisation from di-isopropyl ether gave the product (1.50 g), mp 102°-103°. (Found: C, 80.4; H, 76.2; N, 12.5. C15H16N2 requires C, 80.3; H, 7.2; N, 12.5%)

Provenance & Evidence