Triethylamine → (E)-Diethyl 2-(4-amino-3-methyl-2-nitrobenzylidene)succinate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-iodo-2-methyl-3-nitrobenzenamine (59 mmol) in dimethylformamide (100 mL) was added diethyl itaconate (13.2 g, 71 mmol), tetrabutylammonium chloride (16.4 g, 59 mmol), triethylamine (236 mmol) and palladium acetate (675 mg, 3 mmol) under nitrogen. The reaction mixture was heated to 80° C. for 2 h. The crude reaction mixture was then filtered, diluted with ether (250 mL), washed with water (2×300 mL). The crude product was purified by flash chromatography using 20% ethyl acetate in hexane to give 8.5 g of the title compound. 1H NMR (500 MHz, CDCl3): in δ 7.58 (s, 1 H), 7.10 (d, J=8.5 Hz, 1 H), 6.73 (d, J=8.5 Hz, 1 H), 4.24-4.15 (m, 4H), 3.40 (s, 2 H), 2.06 (s, 3 H), 1.30-1.23 (m, 6 H).

Provenance & Evidence