Maleic Anhydride → HCID 18873878, compound

HRID 2201639Notes

Reaction equation

HRID 2201639 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[C:9]1(=[O:15])[O:14][C:12](=[O:13])[CH:11]=[CH:10]1>O1CCCC1>[NH2:7][C:3]1[CH:2]=[C:1]([NH:8][C:9](=[O:15])/[CH:10]=[CH:11]\[C:12]([OH:14])=[O:13])[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 7935M-Phenylenediamine

Product 1

HCID 18873878HCID 18873878, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, into a reaction vessel were charged 9.96 g (92 mmol) of 1,3-phenylenediamine and 250 ml of tetrahydrofuran. A solution prepared by dissolving 9.03 g (92 mmol) of maleic anhydride in 27 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 separated by filtration, and the filtrate was condensed to dryness, to obtain 16.68 g of coarse (2Z)-4-[(3-aminophenyl)amino]-4-oxo-2-butenoic acid. To 16.68 g of coarse (2Z)-4-[(3-aminophenyl)amino]-4-oxo-2-butenoic acid was added 450 ml of tetrahydrofuran, and the mixture was refluxed with heating for 1 hour, then, the deposited crystal was isolated by hot filtration, and dried to obtain 7.58 g of coarse ((Z)-3-(3-aminophenylcarbamoyl)acrylic acid. Further, to this crystal was added 30 ml of methanol, and the mixture was stirred at room temperature for 1 hour, then, the deposited crystal was isolated by filtration, and dried to obtain 6.94 g of (2Z)-4-[(3-aminophenyl)amino]-4-oxo-2-butenoic acid as a yellow-white solid. Yield: 36.5%.

Workup

  1. customA solution prepared
  2. additionwas dropped into
  3. temperaturethis under cooling with ice over a period of about 1 hour
  4. customAfter completion of the reaction
  5. customthe deposited crystal was separated by filtration
  6. customcondensed to dryness

Sources & evidence

ORD record
ord-bd010415bea344efa0cfa8a130ce68ee
Source dataset
uspto-grants-2016_06
Patent number
US09365497B2

Reaction notes

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