Ethanol → Ethyl Pyridazine-4-carboxylate

HRID 2243886

Reaction equation

HRID 2243886 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=[O:8])=[CH:3][N:2]=1.OS(O)(=O)=O.[CH2:15](O)[CH3:16]>>[CH2:15]([O:8][C:7]([C:4]1[CH:5]=[CH:6][N:1]=[N:2][CH:3]=1)=[O:9])[CH3:16]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 2761046Pyridazine-4-carboxylic Acid

Product 1

HCID 10855652Ethyl Pyridazine-4-carboxylateYield 79%

Procedure

To pyridazine-4-carboxylic acid (1.0 g, 8.1 mmol) in ethanol (10 mL) was added concentrated H2SO4 (4.2 mL) and then heated at reflux for 5 hours. The reaction mixture was cooled, concentrated in vacuo and basified with saturated Na2CO3. After filtration, the aqueous was extracted with ethyl acetate, dried over anhydrous Na2SO4, filtered and concentrated to give the title product as a dark yellow oil (970 mg, 79%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated in vacuo
  5. filtrationAfter filtration
  6. extractionthe aqueous was extracted with ethyl acetate
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b84e4f7eedb348819d43d40a83292036
Source dataset
uspto-grants-2010_03
Patent number
US07678796B2

Linked notes

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