Hydrochloric Acid → 5-Fluoromethoxypyridine-2-carboxylic acid

HRID 1842203Notes

Reaction equation

HRID 1842203 reaction equation
[OH-].[Na+].[F:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([O:14]C)=[O:13])=[N:10][CH:11]=1.Cl.[Cl-].[Na+]>O1CCCC1.O.C(OCC)(=O)C.O>[F:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([OH:14])=[O:13])=[N:10][CH:11]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 57827265Methyl 5-fluoromethoxypyridine-2-carboxylate

Product 1

HCID 574758705-Fluoromethoxypyridine-2-carboxylic acidYield 48.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

5 N sodium hydroxide (81 μL) was added to a solution containing methyl 5-fluoromethoxypyridine-2-carboxylate (50 mg) in tetrahydrofuran/water (2 mL, 3/1), and the mixture was stirred at room temperature for 10 minutes. Water (1 mL) was added to the reaction solution, followed by further stirring for 20 minutes. The reaction solution was made acidic with 5 N hydrochloric acid. Ethyl acetate and a saturated sodium chloride solution were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the insoluble matter was separated by filtration. The filtrate was concentrated to obtain the title compound (22.6 mg).

Workup

  1. stirringby further stirring for 20 minutes
  2. customthe organic layer was separated
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe insoluble matter was separated by filtration
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-44f7cdde34f848cea7e897ba83dd6072
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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