Dimethylformamide → Methyl 2-acetamido-5-chlorocinnamate

Participants

Reaction Steps

To a 200-ml flask were successively charged 40 ml of N,N-dimethylformamide (hereinafter abbreviated as DMF), 20 g (0.0677 mole) of 2-acetylamino-5-chloroiodobenzene, 5.94 g (0.069 mole) of methyl acrylate, 6.94 g (0.0846 mole) of anhydrous sodium acetate, 10 mg of palladium chloride and 30 mg of triphenylphosphine in this order. This mixture was stirred at 130° to 135° C. for 3 hours and poured into 200 ml of water, and then a large amount of crystal precipitated. This crystal was filtered off, thoroughly washed with water and dried in vacuo to obtain 14.1 g of methyl 2-acetylamino-5-chlorocinnamate. The yield was 82.2% of the theoretical value, and the melting point was 172° to 174° C. The nuclear magnetic resonance spectrum (1H-NMR) and infrared absorption spectrum (IR) of this compound were as follows:

Provenance & Evidence