Dimethylformamide → 4-Nitroaniline

Participants

Reaction Steps

Into a 300 mL four-necked flask, 2-iodo-4-nitroaniline (22.5 g, 85.4 mmol), bis(triphenylphosphine)palladium dichloride (1.20 g, 1.71 mmol), and copper iodide (0.651 g, 3.42 mmol) were charged, and nitrogen substitution was carried out, and then diethylamine (43.7 g, 598 mmol) and N,N-dimethylformamide (128 mL) were added thereto, followed by addition of the above-described t-butyl N-propargylamino-N-t-butoxycarbonyl acetate while stirring with ice-cooling, and further stirring at room temperature for 20 hours. After completion of the reaction, 1 L of ethyl acetate was added thereto, and then washing with 150 mL of a 1 mol/L ammonium chloride aqueous solution was carried out three times and washing with 150 mL of a saturated sodium chloride aqueous solution was carried out once, followed by drying by magnesium sulfate. Thereafter, the solvent was removed by evaporation under reduced pressure to precipitate a solid material, and then the solid material was dissolved in 200 mL of ethyl acetate, followed by addition of 1 L of hexane to carry out recrystallization. The solid material was collected by filtration and dried under reduced pressure, thereby to obtain a yellow solid material of 2-{3-(N-t-butoxycarbonyl-N-t-botxycarbonylmethylamino)-1-propynyl)}-4-nitroaniline (compound (A7)). The total amount of yield was 23.0 g, and the yield rate was 66%.

Provenance & Evidence