4-Methyl-8-(trimethylsilyl)-5,6,7,8-tetrahydroquinoline → HCID 178506787, compound

Participants

Reaction Steps

A mixture of a 1.55 molar solution of n-butyl lithium in hexane (12.9 ml, 20 mM) and THF (10 ml), maintained at 5° was treated with a solution of 5,6,7,8-tetrahydro-8-trimethylsilyl-4-methylquinoline (4.34 g, 20 mM) to obtain 5,6,7,8-tetrahydro-8-lithio-8-trimethylsilyl-4-methyl-quinoline. After 0.5 hour a solution of methyl isothiocyanate (1.46 g, 20 mM) in THF (10 ml) was added and after a further 0.5 hour the mixture was quenched with N hydrochloric acid (50 ml). Ether was added and the aqueous layer was separated, adjusted to pH10 and extracted with dichloromethane(2×50 ml). The organic extract was dried, evaporated, dissolved in ethyl acetate and passed through a short pad of silica. Evaporation of the eluate followed by recrystallisation from ethyl acetate gate the title compound (2.4 g) m.p. 151°-3°. The hydrochloride (from propan-2-ol) had m.p. 240°-5°(d) (Found: C,56.5; H,6.6; N,10.6% C12H16N2SHCl requires C,56.1; H,6.7; N,10.9%).

Provenance & Evidence