Methanol → HCID 86708818, compound

HRID 2179489Notes

Reaction equation

[C:1]1([NH2:8])[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.CO.[C:11]1(=[O:17])[O:16][C:14](=[O:15])[CH:13]=[CH:12]1>O1CCCC1>[CH3:14][OH:15].[NH2:7][C:4]1[CH:5]=[CH:6][C:1]([NH:8][C:11](=[O:17])/[CH:12]=[CH:13]\[C:14]([OH:16])=[O:15])=[CH:2][CH:3]=1

Participants

Conditions

Temperature: 5 °C

Procedure

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).

Workup

customA solution prepared
additionwas dropped into
temperaturethis under cooling with ice over a period of 1 hour
customAfter completion of the reaction
temperaturethe temperature thereof was raised to room temperature
customthe deposited solid was isolated by filtration
washwashed with 50 ml of methanol
customThe resultant solid was dried under reduced pressure at 40° C.

Sources & evidence

ORD record: ord-4e62e0b837904aff8e73d6816c93f6d1
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09068055B2

Reaction notes

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