Hydrochloric Acid → 1-(4-Bromo-2,5-difluorophenyl)-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylic acid

HRID 1805576Notes

Reaction equation

HRID 1805576 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12](=[O:17])[C:11]([C:18]([O:20]C)=[O:19])=[N:10]2)=[C:4]([F:22])[CH:3]=1.[OH-].[Na+].Cl>CCO>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12](=[O:17])[C:11]([C:18]([OH:20])=[O:19])=[N:10]2)=[C:4]([F:22])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58072213Methyl 1-(4-bromo-2,5-difluorophenyl)-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylate

Product 1

HCID 580723251-(4-Bromo-2,5-difluorophenyl)-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylic acidYield 101.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 1-(4-bromo-2,5-difluorophenyl)-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylate (25 g, 68 mmol) and 2 M NaOH aqueous solution (68 mL) in EtOH (68 mL) was stirred at room temperature overnight. The solvent was removed by evaporation and resulting aqueous solution was acidified by 6 M HCl aqueous solution (12 mL). The precipitate was collected by filtration and azeotroped with toluene to give the title compound (25 g, 100% yield) as a brown solid: LC-MS (ESI) m/z 376 [M+H]+.

Workup

  1. customThe solvent was removed by evaporation
  2. customresulting aqueous solution
  3. filtrationThe precipitate was collected by filtration
  4. customazeotroped with toluene

Sources & evidence

ORD record
ord-f6159390cc89409fa3ef4d97e14a09ab
Source dataset
uspto-grants-2013_01
Patent number
US08354411B2

Reaction notes

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