Water → 2-phenyl-2,3-dihydrophthalazine-1,4-dione

HRID 1723323Notes

Reaction equation

HRID 1723323 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[C:12]1([NH:18][NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(=O)C.[Na+].O>C(O)(=O)C>[C:12]1([N:18]2[NH:19][C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 7516PhenylhydrazineHCID 517045Sodium Acetate

Product 1

HCID 2257382-phenyl-2,3-dihydrophthalazine-1,4-dioneYield 58%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of phthalic anhydride (0.02 mol) and phenyl hydrazine (0.04 mol) in 95 percent acetic acid (70 ml.) was heated to reflux for 24 hours in the presence of a catalytic amount of sodium acetate (0.4 g). Water was added to the mixture and the precipitate collected. The precipitate was washed with water, agitated with 2 percent aqueous solution of sodium hydroxide and filtered. The filtrate was acidified with concentrated hydrogen chloride. The precipitate was collected and recrystallized from ethyl acetate to produce the product, 2-phenyl-2,3-dihydrophthalazine-1,4-dione.

Workup

  1. temperaturewas heated
  2. customthe precipitate collected
  3. washThe precipitate was washed with water
  4. filtrationfiltered
  5. customThe precipitate was collected
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-20347d331fd240689de4d23cb62d4932
Source dataset
uspto-grants-1989_08
Patent number
US04861778

Reaction notes

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