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

HRID 217706

Reaction equation

HRID 217706 reaction equation
Cl.Cl.[NH2:3][NH2:4].[CH3:5][C:6]1[C:7](=O)[O:8][C:9](=[O:12])[C:10]=1[CH3:11]>O>[CH3:5][C:6]1[C:7](=[O:8])[NH:3][NH:4][C:9](=[O:12])[C:10]=1[CH3:11]

Participants

4

Reactant 2

HCID 13010Dimethylmaleic anhydrideHCID 17548Hydrazine, dihydrochloride

Product 1

HCID 2422804,5-Dimethylpyridazine-3,6-diolYield 62.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Hydrazine dihydrochloride (83.6 g) was dissolved in water (20 ml) and heated to 100° C., and 3,4-dimethylfuran-2,5-dione (100.4 g) was introduced while stirring. Then the mixture was heated to reflux for 3 h. Subsequently, the precipitate formed was filtered off with suction, washed with water and dried. The residue was suspended in EA (2 l), filtered off with suction and dried. 69.7 g of the title compound were obtained. LC-MS rt: 0.19 min[M+H]+: 141.1 (met. b)

Workup

  1. temperatureThen the mixture was heated
  2. temperatureto reflux for 3 h
  3. customSubsequently, the precipitate formed
  4. filtrationwas filtered off with suction
  5. washwashed with water
  6. customdried
  7. filtrationfiltered off with suction
  8. customdried

Sources & evidence

ORD record
ord-6a40094369a44c53991baf5d098a651f
Source dataset
uspto-grants-2012_06
Patent number
US08198272B2

Linked notes

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