Methanol → HCID 46311240, compound

HRID 384117Notes

Reaction equation

HRID 384117 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[C:5]([F:11])=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:14]O>S(=O)(=O)(O)O>[CH3:14][O:9][C:8]([C:6]1[C:5]([F:11])=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1)=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 447547876-Chloro-3-fluoropyridine-2-carboxylic acid

Product 1

HCID 46311240HCID 46311240, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 6-chloro-3-fluoropyridin-2-carboxylic acid (250 mg) in methanol (3 ml), 0.3 ml of concentrated sulfuric acid was added, and the reaction solution was heated to reflux for 2.5 hours. The reaction solution was cooled, and then the solvent was distilled off under reduced pressure. To the residue obtained was added 1N aqueous sodium hydroxide, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford the title compound as a white solid.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureto reflux for 2.5 hours
  3. temperatureThe reaction solution was cooled
  4. distillationthe solvent was distilled off under reduced pressure
  5. customTo the residue obtained
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe combined organic layers were washed with a saturated saline solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f3b65c4193f94445984acb887c6a9c9b
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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