Diethylamine → 4-Nitroaniline

Participants

Reaction Steps

Into a 200 mL four-necked flask, 2-iodo-4-nitroaniline (8.72 g, 33.0 mmol), bis(triphenylphosphine)palladium dichloride (0.463 g, 0.660 mmol) and copper iodide (0.251 g, 1.32 mmol) were charged, and nitrogen substitution was carried out, and then diethylamine (16.9 g, 231 mmol) and N,N-dimethylformamide (50 mL) were added thereto. While stirring with ice-cooling, the above-described t-butyl N-t-butoxycalpropargylglycine (9.69 g, 36.0 mmol) dissolved in N,N-dimethylformamide (16 mL) was added, followed by stirring at room temperature for 16 hours. After completion of the reaction, 500 mL of ethyl acetate was added, and then washing with 100 mL of a 1 mol/L ammonium chloride aqueous solution was carried out three times and washing with 100 mL of a saturated sodium chloride aqueous solution was carried out once, followed by drying by magnesium sulfate. Then, the solvent was removed by evaporation under reduced pressure and the residual oil material was purified by silica gel column chromatography, thereby to obtain a yellow solid of 2-{4-(N-t-butoxycarbonylamino)-4-(t-butoxycarbonyl)-1-butynyl)}-4-nitroaniline (compound (B6)). The total amount of yield was 5.54 g, and the yield rate was 41%.

Provenance & Evidence