Hydrochloric Acid → HCID 14620978, compound

Participants

Reaction Steps

To a solution of 5,6,7,8-tetrahydro-3-methylquinoline (3g) in THF (20ml) at 0° C under nitrogen was added 1.7 molar n-BuLi/hexane solution (12ml) followed by benzonitrile (2ml). The mixture was stirred at ambient temperature 1/2h then 2N HCl was added and the mixture was stirred a further 15 min. The aqueous layer was separated and washed with ether then basified and extracted with chloroform. The extracts were dried (MgSO4) and evaporated. The product was purified by chromatography, first on fluorisil with chloroform and them on silica with 2% MeOH/CHCl3 as eluant. The product was converted into the hydrochloride in propan-2-ol with a Et2O/HCl solution and allowed to crystallise to give 8-benzoyl-5,6,7,8-tetrahydro-3-methylquinoline hydrochloride (1.5g) m.p. 137°-40° C. (Found: C, 70.7; H, 6.5; N, 4.8. C17H17NO.HCl requires C, 70.95; H, 6.3; N, 4.9%.

Provenance & Evidence