Diethyl (ethoxymethylene)malonate → Diethyl 2-(6-trifluoromethyl-2-pyridylaminomethylene)malonate

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-amino-6-trifluoromethylpyridine (15.0 g, 92.5 mmol) and diethyl ethoxymethylenemalonate (18.5 mL, 20.0 g, 92.5 mmol) in 1,4-dioxane (30 mL) was stirred at 100° C. for 48 h. Upon cooling to room temperature, 2-[(6-trifluoromethylpyridin-2-ylamino)methylene]malonic acid diethyl ester precipitated from solution, which was separated by filtration, washed with diethyl ether and air-dried (27.2 g, 89%): δH (400 MHz, CDCl3) 1.35 (3H, t, J 7.2), 1.39 (3H, t, J 7.0), 4.28 (2H, q, J 7.2), 4.33 (2H, q, J 7.2), 7.03 (1H, d, J 8.2), 7.38 (1H, d, J 7.4), 7.82 (1H, t, J 8.1), 9.12 (1H, d, J 12.9), 11.20 (1H, d, J 12.5). m/z (ES+) 333 [MH]+, 287 [M-EtO]+

Provenance & Evidence