Dimethylmaleic anhydride → 4,5-Dimethylpyridazine-3,6-diol

HRID 447104

Reaction equation

HRID 447104 reaction equation
Cl.[NH2:2][NH2:3].[CH3:4][C:5]1=[C:6]([CH3:12])[C:7]([O:9][C:10]1=O)=[O:8]>O>[CH3:4][C:5]1[C:10](=[O:9])[NH:2][NH:3][C:7](=[O:8])[C:6]=1[CH3:12]

Participants

4

Reactant 2

HCID 13010Dimethylmaleic anhydrideHCID 115031Hydrazinium chloride

Product 1

HCID 2422804,5-Dimethylpyridazine-3,6-diolYield 99.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hydrazine hydrochloride (58 g, 552 mmol) is dissolved in hot water (300 mL) and dimethyl maleic anhydride (58 g, 460 mmol) is added in portions and the suspension stirred at reflux for 16 h. The suspension is cooled down to room temperature and the precipitate is filtered, washed with water and dried at 40° C. under vacuum to yield 4,5-dimethyl-1,2-dihydro-pyridazine-3,6-dione (36) (64 g, 99%).

Workup

  1. temperatureat reflux for 16 h
  2. filtrationthe precipitate is filtered
  3. washwashed with water
  4. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-0327013cf966424c9a9f534b8b90572f
Source dataset
uspto-grants-2013_07
Patent number
US08481542B2

Linked notes

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