Diethyl (ethoxymethylene)malonate → Diethyl 2-[(3,4-dimethoxyanilino)methylidene]propanedioate

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Reaction Steps

To a solution of 3,4-dimethoxyaniline (100 g, 0.65 mol) in 130 ml of N,N-dimethylformamide was added diethyl ethoxymethylene malonate (141.2 g, 0.65 mol). The mixture was stirred at room temperature for 21 hours. The solvent was evaporated in vacuo and the residual dark brown oil was recrystallized from 1.6 l cyclohexane and 50 g of activated carbon to give 150.5 g of desired product. Extraction of the carbon with hot cyclohexane gave another 27.1 g of product. Total yield 177.6 g, melting point 57°-59° C.

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