Acetic Acid → 5,8-Difluoro-2,3-dihydrophthalazine-1,4-dione

HRID 593929Notes

Reaction equation

HRID 593929 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[C:4](=O)[O:5][C:6]2=[O:12].C([O-])(=O)C.[Na+].C(O)(=O)C.[NH2:23][NH2:24]>O>[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[C:4](=[O:5])[NH:23][NH:24][C:6]2=[O:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9321HydrazineHCID 5139183,6-Difluorophthalic anhydrideHCID 517045Sodium Acetate

Product 1

HCID 667320095,8-Difluoro-2,3-dihydrophthalazine-1,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4,7-difluoroisobenzofuran-1,3-dione (1.00 g, 5.43 mmol) and sodium acetate (0.535 g, 6.52 mmol) was added water (14 mL), acetic acid (7.15 ml, 125 mmol) and hydrazine (0.205 ml, 6.52 mmol) (slowly). A water condenser was attached and the mixture was heated to reflux for 20 hours. Cooled to RT and filtered the resulting solid. Washed with water and dried to yield 5,8-difluoro-2,3-dihydrophthalazine-1,4-dione as a white solid. MS m/z=199 [M+1]+. Calc'd for C8H4F2N2O2: 198.13.

Workup

  1. customA water condenser was attached
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 20 hours
  4. filtrationfiltered the resulting solid
  5. washWashed with water
  6. customdried

Sources & evidence

ORD record
ord-6a2011ab5e9d47c7b2be16fe55817138
Source dataset
uspto-grants-2016_01
Patent number
US09242961B2

Reaction notes

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