Dimethylformamide → HCID 53659605, compound

Participants

Reaction Steps

To a 200-ml flask were added 40 ml of DMF, 20 g (0.0717 mole) of 2-acetylamino-5-fluoroiodobenzene, 5.85 g (0.0812 mole) of acrylic acid, 7.77 g (0.0947 mole) of anhydrous sodium acetate, 10 mg of palladium chloride and 30 mg of triphenylphosphine. This mixture was stirred at 125° to 130° C. for 3 hours and poured into 200 ml of water, and then a large amount of crystal precipitated. Sodium hydroxide was added to this aqueous solution containing the crystal while stirring the solution as it was, until the pH of the solution became 9.0 to obtain a uniform solution. Thereafter, 2 g of activated carbon was added to the solution, and after stirring at room temperature for 15 minutes, the insoluble matter was filtered off. The filtrate was acidified to a pH of 4.0 with conc. hydrochloric acid, and then white crystal precipitated. This crystal was filtered off and vacuum-dried to obtain 12.6 g of 2-acetylamino-5-fluorocinnamic acid. The yield was 78.5% of the theoretical value, and the melting point was 232° to 233° C. The 1H-NMR and IR of this compound were as follows:

Provenance & Evidence