Hydrochloric Acid → HCID 57950214, compound

Participants

Reaction Steps

8.73 g of sodium hydride (55% oil dispersion) was suspended in 100 ml of 1,4-dioxane. Into this, 32.03 g of diethyl malonate was added dropwise over a period of about 1 hour at 60° C. under a nitrogen atmosphere. The mixture was stirred at the same temperature further for 0.5 hours, then, to the mixture was added 8.26 g of copper chloride (I). Thereafter, into the mixture, a solution prepared by dissolving 12.23 g of 2,3-dichloropyridine in 50 ml of 1,4-dioxane was added dropwise at 80° C. The mixture was stirred for 22.5 hours under reflux with heating. The reaction mixture was allowed to cool to room temperature, and to the reaction mixture was added 15 ml of concentrated hydrochloric acid. To the mixture were added water and ethyl acetate, and the mixture was filtrated through celite. The filtrate was liquid-separated. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. 46.65 g of the resultant residue was subjected to silica gel column chromatography, to obtain 3.90 g of diethyl (3-chloro-2-pyridyl)malonate.

Provenance & Evidence