Hydrochloric Acid → HCID 20348480, compound

Participants

Reaction Steps

3-Methyl-8-cyano-5,6,7,8-tetrahydroquinoline (1.7 g., 0.01 m.) and thioacetamide (1.5 g., 0.02 m.) were dissolved in dimethylformamide (50 ml.), and the solution saturated with dry hydrogen chloride gas and then heated on a steam bath for 4 hours. The cooled reaction mixture was poured onto water (200 ml.), washed with ethyl acetate (2 × ml) and the extracts discarded. The aqueous solution was adjusted to pH 10.0 with 46% sodium hydroxide and extracted into methylene chloride (2 × 200 ml.). The combined extracts were dried (sodium sulphate), evaporated i vacuo and the residual oil triturated with isopropanol and filtered. Recrystallization from benzene gave the title compound as pale yellow needles (1.3 g., 63%) m.p. 149°.

Provenance & Evidence