Lithium Hydroxide → HCID 86708823, compound

HRID 2201652Notes

Reaction equation

HRID 2201652 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.[C:9]1(=[O:15])[O:14][C:12](=[O:13])[CH:11]=[CH:10]1.[OH-].[Li+:17]>O1CCCC1.O>[NH2:7][C:4]1[CH:5]=[CH:6][C:1]([NH:8][C:9](=[O:15])/[CH:10]=[CH:11]\[C:12]([O-:14])=[O:13])=[CH:2][CH:3]=1.[Li+:17]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 7814P-PhenylenediamineHCID 7923Maleic Anhydride

Product 1

HCID 86708823HCID 86708823, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, into a reaction vessel were charged 13.23 g (122.4 mmol) of 1,4-phenylenediamine and 225 ml of tetrahydrofuran. A solution prepared by dissolving 8.00 g (81.6 mmol) of maleic anhydride in 24 ml of tetrahydrofuran was dropped into this under cooling with ice over a period of 2 hours, then, the mixture was stirred at room temperature for 3 hours. After completion of the reaction, a solution prepared by dissolving 1.99 g (81.6 mmol) of 98% lithium hydroxide in 17.95 g of water was dropped at room temperature over a period of 30 minutes, and the mixture was stirred at room temperature for 1 hour. Thereafter, the solvent was distilled off under reduced pressure to obtain a residue to which 200 ml of 2-propanol was added, and the mixture was stirred at room temperature overnight. Thereafter, the deposited solid was isolated by filtration, and washed with 50 ml of 2-propanol. The resultant solid was dried under reduced pressure at 45° C. for 5 hours, to obtain 13.03 g of lithium (2Z)-4-[(4-aminophenyl)amino]-4-oxo-2-butenoate as a pate brown-white solid. Yield: 75.3%

Workup

  1. customA solution prepared
  2. additionwas dropped into
  3. temperaturethis under cooling with ice over a period of 2 hours
  4. customAfter completion of the reaction
  5. customa solution prepared
  6. additionwas dropped at room temperature over a period of 30 minutes
  7. stirringthe mixture was stirred at room temperature for 1 hour
  8. distillationThereafter, the solvent was distilled off under reduced pressure
  9. customto obtain a residue to which 200 ml of 2-propanol
  10. additionwas added
  11. stirringthe mixture was stirred at room temperature overnight
  12. customThereafter, the deposited solid was isolated by filtration
  13. washwashed with 50 ml of 2-propanol
  14. customThe resultant solid was dried under reduced pressure at 45° C. for 5 hours

Sources & evidence

ORD record
ord-bc548184f4634e33bf124b78e3cebde7
Source dataset
uspto-grants-2016_06
Patent number
US09365497B2

Reaction notes

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