Hydrazine Sulfate → 4,5-Dichloro-3-hydroxypyridazine

HRID 2381296Notes

Reaction equation

HRID 2381296 reaction equation
S(O)(O)(=O)=O.[NH2:6][NH2:7].[Cl:8][C:9]1[C:10](=O)[O:11][CH:12](O)[C:13]=1[Cl:14].C([O-])(=O)C.[Na+]>O>[Cl:8][C:9]1[C:10](=[O:11])[NH:6][N:7]=[CH:12][C:13]=1[Cl:14]

Participants

5

Reactant 3

HCID 24842Hydrazine SulfateHCID 91487Mucochloric acid lactoneHCID 517045Sodium Acetate

Product 1

HCID 732474,5-Dichloro-3-hydroxypyridazineYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hydrazine sulfate (305.7 g, 2.35 mol) was added to a solution of 3,4-dichloro-5-hydroxy-5H-furan-2-one (419 g, 2.48 mol) and sodium acetate (212 g, 2.58 mol) in water (600 mL). The mixture was stirred at reflux for 4 h. After filtration and evaporation, the residual solid was recrystallized from ethanol to afford 4,5-dichloropyridazin-3(2H)-one (216 g, 67%) as an off-white solid. LC-MS 165 [M+H+].

Workup

  1. temperatureat reflux for 4 h
  2. filtrationAfter filtration and evaporation
  3. customthe residual solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-f9a5f98f03594cc0b2262fcfb24eb37d
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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