Diethyl Ether → HCID 12818620, compound

Participants

Reaction Steps

To a solution of 20.1 g. (0.1 mole) of 2-cyclohexylaminonicotinonitrile in 1000 ml. of anhydrous ethyl ether was added 7.5 g. (0.05 mole) of ethyl malonyl chloride. The mixture was stirred at room temperature for 1 hour. The mixture was filtered and the filtrate was evaporated in a rotary evaporator. The residue was triturated with 30 ml. of ether and was filtered. The filtrate was evaporated and this residue was added to a solution of 2.3 g. (0.1 g. atom) of sodium in 250 ml. of ethanol. The mixture was stirred at room temperature for 5 minutes, diluted with water and was acidified with conc. hydrochloric acid. The solution was cooled in ice and the precipitate which formed was collected, air dried and was recrystallized twice from ethyl acetate to afford 1.0 g. of the title product, m.p. 172°-175° C.

Provenance & Evidence