P-Phenylenediamine → HCID 86708822, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, into a reaction vessel were charged 13.23 g (122.4 mmol) of 1,4-phenylenediamine and 225 ml of tetrahydrofuran. A solution prepared by dissolving 8.00 g (81.6 mmol) of maleic anhydride in 24 ml tetrahydrofuran was dropped into this under cooling with ice over a period of 2 hours, then, the mixture was stirred at room temperature for 3 hours. After completion of the reaction, 17.99 g (81.6 mmol) of a 25% potassium hydroxide aqueous solution was dropped under cooling with ice over a period of 30 minutes, and the mixture was stirred at room temperature for 2 hours. Thereafter, the solvent was distilled off under reduced pressure to obtain a residue to which 200 ml of tetrahydrofuran was added, and the mixture was stirred at 40° C. for 1 hour. After cooling to room temperature, the deposited solid was isolated by filtration, and washed with 50 ml of tetrahydrofuran. The resultant solid was dried under reduced pressure at 50° C. for 5 hours, to obtain 19.79 g of potassium (2Z)-4-[(4-aminophenyl)amino]-4-oxo-2-butenoate mono-hydrate as a red-brown solid. Yield: 92.5%

Provenance & Evidence