P-Phenylenediamine → HCID 86708817, compound

HRID 2179488Notes

Reaction equation

HRID 2179488 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.[C:9]1(=[O:16])[O:15][C:13](=[O:14])[CH:12]=[C:10]1[CH3:11]>O1CCCC1>[NH2:7][C:4]1[CH:5]=[CH:6][C:1]([NH:8][C:13](=[O:14])/[CH:12]=[C:10](/[CH3:11])\[C:9]([OH:16])=[O:15])=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 7814P-PhenylenediamineHCID 12012Citraconic Anhydrides

Product 1

HCID 86708817HCID 86708817, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, into a reaction vessel were charged 10.0 g (92.5 mmol) of 1,4-phenylenediamine and 250 ml of tetrahydrofuran. A solution prepared by dissolving 10.4 g (92.5 mmol) of citraconic anhydride in 20 ml of tetrahydrofuran was dropped into this under cooling with ice over a period of 20 minutes, then, the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the deposited crystal was isolated by filtration, and dried to obtain 15 g of coarse (2Z)-4-[(4-aminophenyl)amino]-2-methyl4-oxo-2-butenoic acid. Five grams (5 g) of coarse (2Z)-4-[(4-aminophenyl)amino]-2-methyl4-oxo-2-butenoic acid was repulped with 2-propanol and methanol each at 50° C. for 3 hours, then, repulped with chloroform, to obtain 13.1 g of (2Z)-4-[(4-aminophenyl)amino]-2-methyl-4-oxo-2-butenoic acid as a yellow solid. Yield: 64.3%.

Workup

  1. customA solution prepared
  2. additionwas dropped into
  3. temperaturethis under cooling with ice over a period of 20 minutes
  4. customAfter completion of the reaction
  5. customthe deposited crystal was isolated by filtration
  6. customdried

Sources & evidence

ORD record
ord-6320742d14c240cbb3e4c78312e53529
Source dataset
uspto-grants-2015_06
Patent number
US09068055B2

Reaction notes

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