Methanol → HCID 86708818, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, into a reaction vessel were charged 10.00 g (92.5 mmol) of 1,4-phenylenediamine and 80 ml of methanol. A solution prepared by dissolving 6.05 g (61.6 mmol) of maleic anhydride in 20 ml of tetrahydrofuran was dropped into this under cooling with ice over a period of 1 hour, then, the mixture was stirred at 0 to 10° C. for 3 hours. After completion of the reaction, the temperature thereof was raised to room temperature, the deposited solid was isolated by filtration, and washed with 50 ml of methanol. The resultant solid was dried under reduced pressure at 40° C., to obtain 12.63 g of (2Z)-4-[(4-aminophenyl)amino]-4-oxo-2-butenoic acid methanol solvate as a pale yellow powder. Yield: 86.0%. H1-NMR (270 MHz, DMSO-d6) δp p m: 10.6 (1H, s), 7.3 (2H, d, J=8.9 Hz), 6.5 (2H, d, J=8.9 Hz), 6.5 (1H, d, J=12.5 Hz), 6.3 (1H, d, J=12.2 Hz), 3.2 (3H, s).

Provenance & Evidence