Methanol → HCID 86708818, compound

HRID 2201642Notes

Reaction equation

HRID 2201642 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

5

Reactant 3

HCID 887MethanolHCID 7814P-PhenylenediamineHCID 7923Maleic Anhydride

Product 1

HCID 86708818HCID 86708818, compoundYield 172.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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%.

Workup

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

Sources & evidence

ORD record
ord-18d5b255515c4296a3e2d6cb166d417f
Source dataset
uspto-grants-2016_06
Patent number
US09365497B2

Reaction notes

Loading…