Diisopropylamine → 5,6,7,8-Tetrahydroquinoline-8-carbothioamide

Participants

Reaction Steps

A solution of di-isopropylamine (33.3g, 0.33 mol) in benzene (150 ml) was cooled in ice and treated with 9% w/v butyl-lithium in hexane (237 ml, 0.33 mol). After 45 minutes the solution was treated with 5,6,7,8-tetrahydroquinoline (39.9 g, 0.3 mol) dropwise with stirring. After 1.5 hours trimethylsilyl-isothiocyanate (43.2 ml. 0.3 mol) was added and the resulting solution was allowed to stand at 0° C for 0.5 hours and at room temperature for 1 hour. Water (50 ml.) was added to the solution of 5,6,7,8-tetrahydroquinoline-8-(N-lithio-N-trimethylsilyl) thiocarboxamide causing hydrolysis to 5,6,7,8-tetrahydroquinoline-8-(N-trimethylsilyl)thiocarboxamide and subsequent hydrolysis to the title compound, and the resulting mixture acidified with 2N HCl. The acid solution was separated, washed with ethyl acetate and the pH was adjusted to 9 with solid sodium carbonate. Extraction with chloroform followed by drying of the extract over MgSO4, filtration and evaporation gave a thick gum which crystallised on trituration with n-hexane. Recrystallisation from methanol gave 5,6,7,8-tetrahydroquinoline-8-thiocarboxamide (16g, 30%) m.p. 160°. The hydrochloride was prepared by dissolution of the free base in hot isopropyl alcohol adding ethereal HCl solution and allowing to crystallise. m.p. 263°-4°. (Found: C, 52.6; H, 6.0; N, 12.2. C10H12N2S, HCl requires C, 52.5; H, 5.7; N, 12.3%).

Provenance & Evidence