2-Nitroaniline → Diethyl 2-((2-nitrophenylamino)methylene)malonate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-nitroaniline (20 g, 144.8 mmol) dissolved in 400 ml of dry-ethanol in a 500 ml round bottom flask was added dimethylethoxymethylene malonate (34 g, 159.3 mmol). The solution was heated and refluxed for 6 hrs at 120° C. with stirring. The reaction was monitered by TLC (n-hexane/ethyl acetate=3/1). After completing the reaction and cooling to room temperature, the resulting precipate was collected by filtration, and the residue was washed three times with 100 ml of n-hexane to give 2-[(2-Nitro-phenylamino)-methylene]-malonic acid diethyl ester (31 g, 100.6 mmol, yield 69%).

Provenance & Evidence