Hydrochloric Acid → HCID 58158523, compound

HRID 2095850Notes

Reaction equation

HRID 2095850 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([C:15]([O:17]CC)=[O:16])[C:9]2=[O:20])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([C:15]([OH:17])=[O:16])[C:9]2=[O:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58158591HCID 58158591, compound

Product 1

HCID 58158523HCID 58158523, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 1-(4-fluorophenyl)-5-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate (1.2 g, 4.36 mmol) in methanol (12 mL) was added 1N aqueous sodium hydroxide solution (10 mL, 10 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, and the obtained residue was diluted with ethyl acetate and water and extracted with water. The aqueous layer was treated with 1N hydrochloric acid (20 mL, 20 mmol), and the precipitate was collected by filtration to give a white solid. The white solid was washed with water to give the title compound (730 mg, 68%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe obtained residue was diluted with ethyl acetate and water
  3. extractionextracted with water
  4. filtrationthe precipitate was collected by filtration
  5. customto give a white solid
  6. washThe white solid was washed with water

Sources & evidence

ORD record
ord-67733542ceff469aac91e04fcd092e40
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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