Oxalic Acid → HCID 13200217, compound

Participants

Reaction Steps

A solution of 2-dimethylaminoethanethiol hydrochloride (1.7 g.) in dimethylformamide (25 ml.) was added dropwise to a suspension of sodium hydride (0.5 g.) in a solution of 2-chloro-3-cyclopropylquinoline (2.0 g.) in dimethylformamide (25 ml.) at 0°-5°. The mixture was then heated at 80° for 4 hr. and then poured into ice water (200 ml.) and extracted with ethyl acetate (3×100 ml.). The ethyl acetate extract was washed successively with saturated brine (100 ml.) and water (3×100 ml.), dried (Na2SO4), and the solvent evaporated. The residue was chromatographed on silica gel (Merck 9385, 200 g.) using 10% v/v methanol in ethyl acetate as eluant. The appropriate fraction (monitored by thin layer chromatography) was evaporated, dissolved in methanol, and one equivalent of anhydrous oxalic acid was added. The solvent was evaporated and the residue crystallised from methanol/diethyl ether to give 3-cyclopropyl-2-(2-dimethylaminoethylthio)quinoline hydrogen oxalate, m.p. 158°.

Provenance & Evidence