Ethanol → 5,6-Dihydrofuro[2,3-d]pyridazine-4,7-dione

HRID 42227Notes

Reaction equation

HRID 42227 reaction equation
C[O:2][C:3]([C:5]1[O:6][CH:7]=[CH:8][C:9]=1[C:10]([O:12]C)=O)=O.CCO.O.[NH2:18][NH2:19]>O>[O:6]1[C:5]2[C:3](=[O:2])[NH:18][NH:19][C:10](=[O:12])[C:9]=2[CH:8]=[CH:7]1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 158004Furandicarboxylic acid, dimethyl ester

Product 1

HCID 206213105,6-Dihydrofuro[2,3-d]pyridazine-4,7-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Furan-2,3-dicarboxylic acid dimethyl ester (1.6 g, 8.69 mmol) is added to EtOH (10 mL) and hydrazine hydrate (1.46 mL, 55% in water). Heat the reaction to reflux for 5-6 h. Cool and concentrate in vacuo to form a slurry. Dilute the material with additional H2O and filter the precipitate. Wash with additional H2O. Transfer material from filter to a round bottom flask and add HCl (7.2 mL, 2N in H2O). Heat reaction mixture to reflux for 4 h. Cool and filter the precipitate washing with H2O, to yield the title compound without further purification (930 mg, 70%)

Workup

  1. temperatureHeat
  2. customthe reaction
  3. temperatureto reflux for 5-6 h
  4. temperatureCool
  5. concentrationconcentrate in vacuo
  6. customto form a slurry
  7. filtrationfilter the precipitate
  8. washWash with additional H2O
  9. filtrationTransfer material from filter to a round bottom flask
  10. additionadd HCl (7.2 mL, 2N in H2O)
  11. temperatureHeat
  12. customreaction mixture
  13. temperatureto reflux for 4 h
  14. temperatureCool
  15. filtrationfilter the precipitate
  16. washwashing with H2O

Sources & evidence

ORD record
ord-2ebb0da334174606947c849ab3b2fdde
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Reaction notes

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