P-Phenylenediamine → (2Z)-4-[(4-aminophenyl)amino]-4-oxo-2-butenoic acid
反応式
[C:1]1([NH2:8])[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.[C:9]1(=[O:15])[O:14][C:12](=[O:13])[CH:11]=[CH:10]1>O1CCCC1>[NH2:7][C:4]1[CH:5]=[CH:6][C:1]([NH:8][C:9](=[O:15])/[CH:10]=[CH:11]\[C:12]([OH:14])=[O:13])=[CH:2][CH:3]=1参加物
4
実験手順
Under a nitrogen atmosphere, into a reaction vessel were charged 13.0 g (0.12 mol) of 1,4-phenylenediamine and 140 ml of tetrahydrofuran. A solution prepared by dissolving 11.77 g (0.12 mol) of maleic anhydride in 25 ml of tetrahydrofuran was dropped into this under cooling with ice over a period of about 1 hour, then, the mixture was stirred at room temperature overnight. After completion of the reaction, the deposited crystal was isolated by filtration, and dried to obtain 24.20 g of coarse (2Z)-4-[(4-aminophenyl)amino]-4-oxo-2-butenoic acid as an orange powder. To 24.2 g of coarse (2Z)-4-[(4-aminophenyl)amino]-4-oxo-2-butenoic acid were added 250 ml of tetrahydrofuran and 50 ml of water, and the mixture was stirred at room temperature for 2 hours, then, isolated by filtration, and the filtrated material was washed twice with 20 ml of 50% tetrahydrofuran water. The resultant crystal was dried at 40° C. for 5 hours, to obtain 21.96 g of (2Z)-4-[(4-aminophenyl)amino]-4-oxo-2-butenoic acid mono-hydrate as a yellow-orange powder. Yield: 81.5%.