Methanol → (E)-ethyl 3-(4-acetamido-3-(2-methoxyethoxy)phenylamino)-2-cyanoacrylate

Participants

Reaction Steps

To N-(2-(2-methoxyethoxy)-4-nitrophenyl)acetamide (75 g, 0.295 mol, 1.00 equiv) was added methanol (600 ml), 10% Pd/C (6 g), and glacial acetic acid (60 ml) in a vessel which subject to a closed pressure vessel. Replacement of Kettle access from air to 5 atm hydrogen at room temperature was deployed and reacted for 5 hours. The reaction mixture was filtered, and concentrated. Toluene (440 ml), THF (220 ml), and (E)-ethyl 2-cyano-3-ethoxyacrylate (76 g, 0.497 mol, 1.68 equiv) were added and then refluxed for 16 h. The reaction mixture was cooled to room temperature, filtered, washed and dried with tetrahydrofuran to give 77 g product as off-white solid. MS (ESI) m/z: 347 (M+1).

Provenance & Evidence