Dimethyl Sulfoxide → HCID 13384138, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 6 g of sodium hydride (55-60% in paraffin) in 80 ml of anhydrous dimethyl sulphoxide was stirred for 2 hours at 70° C. A solution of 8.8 g of 1-chloro-3-(6-methyl-2-pyridyl)isoquinoline (prepared as described in Example XI) in anhydrous tetrahydrofuran was added dropwise to the mixture with ice-cooling, to obtain a deep red-coloured reaction mixture. The mixture was stirred for 2 hours at 50° C. and was then extracted with dichloromethane, after addition of ice-water. The organic layer was washed with a saturated aqueous sodium chloride solution and with water and the solvent was then distilled off. The residue was dissolved in diethyl ether and ethereal hydrogen chloride was added to the solution. The precipitate obtained was filtered off and dissolved in water. The solution was made alkaline with aqueous sodium hydroxide and extracted with diethyl ether. The ether was distilled off and the residue was crystallised from a mixture of ethanol and pentane. 3-(-6-Methyl-2-pyridyl)-1-methylsulphinylmethylisoquinoline was obtained, melting point 198.0° -198.5° C. A portion of the base was converted into the hydrochloride which, after crystallisation from isopropyl alcohol, melted at 120°-121° C. (decomp.).

Provenance & Evidence