Hydrochloric Acid → 5-Methoxy-4-oxo-1-phenyl-1,4-dihydropyridazine-3-carboxylic acid

HRID 333736Notes

Reaction equation

HRID 333736 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:19])[C:5]([C:15]([O:17]C)=[O:16])=[N:6][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1.[OH-].[Na+].Cl>CO>[CH3:1][O:2][C:3]1[C:4](=[O:19])[C:5]([C:15]([OH:17])=[O:16])=[N:6][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 89586545Methyl 5-methoxy-4-oxo-1-phenyl-1,4-dihydropyridazine-3-carboxylate

Product 1

HCID 895867345-Methoxy-4-oxo-1-phenyl-1,4-dihydropyridazine-3-carboxylic acidYield 97.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of methyl 5-methoxy-4-oxo-1-phenyl-1,4-dihydropyridazine-3-carboxylate (39.04 g) in methanol (663 mL) was added dropwise 1N sodium hydroxide (300 mL) with stirring under ice-cooling, and the mixture was allowed to warm to room temperature and stirred for 1 hr. 1N Hydrochloric acid (300 mL) was added dropwise with stirring under ice-cooling, and the mixture was stirred at the same temperature for 1 hr. The precipitated crystals were collected by filtration, washed successively with water, ethanol/diisopropyl ether (1/2), and diisopropyl ether, and dried to give the title compound (36.1 g) as pale-yellow crystals.

Workup

  1. temperaturecooling
  2. stirringstirred for 1 hr
  3. stirringwith stirring under ice-
  4. temperaturecooling
  5. stirringthe mixture was stirred at the same temperature for 1 hr
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed successively with water, ethanol/diisopropyl ether (1/2), and diisopropyl ether
  8. customdried

Sources & evidence

ORD record
ord-d7aa22db74f3440a938342de193da510
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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