Hydrazine, dihydrochloride → 4-(Trifluoromethyl)-1,2-dihydropyridazine-3,6-dione

HRID 657928Notes

Reaction equation

HRID 657928 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[C:4](=O)[O:5][C:6](=[O:8])[CH:7]=1.Cl.Cl.[NH2:14][NH2:15]>O>[F:1][C:2]([F:11])([F:10])[C:3]1[C:4](=[O:5])[NH:14][NH:15][C:6](=[O:8])[CH:7]=1

Participants

4

Reactant 2

HCID 17548Hydrazine, dihydrochlorideHCID 27775313-(Trifluoromethyl)furan-2,5-dione

Product 1

HCID 669415854-(Trifluoromethyl)-1,2-dihydropyridazine-3,6-dioneYield 4.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Trifluoromethylfuran-2,5-dione (5 g) was introduced in portions into an already boiling solution of hydrazine dihydrochloride (3.2 g) in water (50 ml). After stirring for 4 h, the mixture was left to stand overnight; the next day, the mixture was refluxed for a further 8 h and left to stand overnight. Then it was dried and the residue was purified by means of preparative chromatography (met. C). The clean fractions were combined, the ACN was drawn off and the residue was freeze-dried. 250 mg of the title compound were obtained. LC-MS rt: 0.23 min [M+H]+: 181.1 (met.b)

Workup

  1. waitthe mixture was left
  2. waitto stand overnight
  3. temperaturethe next day, the mixture was refluxed for a further 8 h
  4. waitleft
  5. waitto stand overnight
  6. customThen it was dried
  7. customthe residue was purified by means of preparative chromatography (met. C)
  8. customthe residue was freeze-dried

Sources & evidence

ORD record
ord-dfe4c3c022484aa890fdf7518fc8a9b2
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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