Benzaldehyde → HCID 86605710, compound

Participants

Reaction Steps

A mixture of ethyl hydrazinoacetate hydrochloride (15.5 g), sodium hydrogen carbonate (8.40 g), water (15 mL) and ethanol (100 mL) was stirred at room temperature for 30 min. Benzaldehyde (10.61 g) was added to the reaction mixture, and after stirring for 1 hr, diethyl ethoxymethylenemalonate (21.6 g) was added. The mixture was heated under reflux for 15 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:3, v/v) to give diethyl [(2-benzylidene-1-(ethoxycarbonylmethyl)hydrazino]methylene}malonate as colorless crystals (8.75 g, yield 23%). The crystals were recrystallized from ethyl acetate-hexane. melting point: 105-106° C.

Provenance & Evidence