Hydrochloric Acid → 4-Hydroxy-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylic acid

HRID 2427783Notes

Reaction equation

HRID 2427783 reaction equation
[OH:1][C:2]1[C:3]([C:15]([O:17]C)=[O:16])=[N:4][N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6](=[O:8])[CH:7]=1.Cl>[OH-].[Na+]>[OH:1][C:2]1[C:3]([C:15]([OH:17])=[O:16])=[N:4][N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6](=[O:8])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54686161Methyl 1,6-dihydro-4-hydroxy-6-oxo-1-phenyl-3-pyridazinecarboxylate

Product 1

HCID 547060644-Hydroxy-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylic acidYield 80%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Methyl 4-hydroxy-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylate (0.8 g, 3.24 mmol) was suspended in sodium hydroxide solution (20 ml of 2.0M) and heated at reflux for 1 hour. The mixture was allowed to cool to room temperature, acidified with 2M hydrochloric acid and extracted with ethyl acetate (3×15 ml). The combined organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated to yield 4-hydroxy-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylic acid as a yellow solid (0.6 g, 80%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. extractionextracted with ethyl acetate (3×15 ml)
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-3019beb2007a4635beeb4aa22edf58ef
Source dataset
uspto-grants-2011_06
Patent number
US07968711B2

Reaction notes

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