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

HRID 2089826Notes

Reaction equation

HRID 2089826 reaction equation
[Br:1][C:2]1[C:3]([F:21])=[C:4]([N:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11](=[O:16])[C:10]([C:17]([O:19]C)=[O:18])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].Cl>CO>[Br:1][C:2]1[C:3]([F:21])=[C:4]([N:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11](=[O:16])[C:10]([C:17]([OH:19])=[O:18])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59436204Methyl 1-(3-bromo-2-fluorophenyl)-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylate

Product 1

HCID 594361901-(3-Bromo-2-fluorophenyl)-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of methyl 1-(3-bromo-2-fluorophenyl)-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylate (4.16 g, 11.7 mmol) in MeOH (46 mL) was added 1 M NaOH aqueous solution (23 mL) at 0° C. The mixture was stirred at room temperature for 1 h. To the solution was added 1 M HCl aqueous solution (23 mL) at 0° C. The mixture was concentrated in vacuo. The precipitates were collected by filtration, washed with water and dried in vacuo at 50° C. to yield the title compound (3.76 g, 94% yield) as a pale yellow solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 3.87 (3H, s), 7.43 (1H, td, J=8.1, 1.5 Hz), 7.76-7.85 (1H, m), 7.98 (1H, ddd, J=8.0, 6.5, 1.3 Hz), 8.86 (1H, s), 14.84 (1H, brs).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with water
  4. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-4489f7e5e86d474ab2b11b652390c948
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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