Hydrochloric Acid → HCID 58158515, compound

HRID 2095867Notes

Reaction equation

HRID 2095867 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16]C)=[O:15])[C:9]2=[O:18])=[C:4]([CH3:19])[CH:3]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:16])=[O:15])[C:9]2=[O:18])=[C:4]([CH3:19])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66968619HCID 66968619, compound

Product 1

HCID 58158515HCID 58158515, compoundYield 186.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of methyl 1-(4-fluoro-2-methylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate (0.40 g, 1.53 mmol) in methanol (9 mL) was added 2N aqueous sodium hydroxide solution (1.15 mL), and the mixture was stirred at room temperature for 3 hr. 6N Hydrochloric acid (0.5 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the obtained residue was washed with hexane/ethyl acetate (=1/1) to give the title compound (704 mg, 85%) as a yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. washthe obtained residue was washed with hexane/ethyl acetate (=1/1)

Sources & evidence

ORD record
ord-68e5b12868324109b740fe3bff82cf23
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

Loading…