N-methyl-2-pyrrolidone → HCID 20158990, compound

Participants

Reaction Steps

A solution of sodium methanethiolate (15 cm3 of a 2.0M solution in methanol) was added at room temperature to a solution of 8-bromo-6-[2,6-dimethylpyrid-3-yl]-2-(1H)-quinolone (0.50 g) and cuprous iodide (0.15 g) in N-methyl-2-pyrollidone (12 cm3). After heating at 160° for 48 hours the cooled mixture was diluted with chloroform (100 cm3) and water (50 cm3). The separated aqueous phase was further extracted with chloroform (3×50 cm3), and the combined and dried (MgSO4) chloroform extracts were evaporated in vacuo to given an oil which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with chloroform. Combination and evaporation of appropriate fractions gave a solid which was recrystallised from ethyl acetate to afford 6-[2,6-dimethyl-pyrid-3-yl]-8-thiomethyl-2-(1H)-quinolone 0.25 H2O, m.p. 146.5°-148.5° (0.04 g).

Provenance & Evidence