Ethyl-alpha-carbethoxy-4-dimethylamino-2-nitrocinnamate → Ethyl-alpha-carbethoxy-4-methylamino-2-nitrocinnamate

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Reaction Steps

The cinnamic ester (1) (5.0 g, 14.8 mmol) was dissolved in 100 mL of acetic acid and 7.6 g (17.2 mmol) of lead tetracetate was added. After allowing the mixture to stir for one hour at room temperature, the solvent was removed. Toluene (100 mL) was added and the slurry concentrated, then 100 mL of chloroform (CHCl3) was added, the solid broken up thoroughly, and the solution decanted. Chloroform (100 mL) was added to the solid and the mixture refluxed briefly, filtered, and the filtrate combined with the previous CHCl3 solution. After concentrating the organic solution the residue was chromatographed on 350 g of silica gel eluting with 1:19 (v/v) acetone:CHCl3. Fractions 83-140 (15 mL/fraction) were combined and concentrated to yield the product which was crystallized from CH2Cl2 (3.45 g, 72%), m.p. 113°-114° C.

Provenance & Evidence