Sodium Hydroxide → 3-Methoxypyridine-2-carboxylic acid

HRID 1842260Notes

Reaction equation

HRID 1842260 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[C:6]([C:11]([O:13]C)=[O:12])=[N:7][CH:8]=[CH:9][CH:10]=1>CO>[CH3:3][O:4][C:5]1[C:6]([C:11]([OH:13])=[O:12])=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20474189Methyl 3-methoxypyridine-2-carboxylate

Product 1

HCID 132095403-Methoxypyridine-2-carboxylic acidYield 18.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 5 N sodium hydroxide solution (147 μL) was added to a solution of methyl 3-methoxypyridine-2-carboxylate (112 mg) in methanol (2 mL), and the mixture was stirred at room temperature overnight. The excess of methanol was evaporated under reduced pressure, and the residue was diluted with water. The aqueous layer was washed with ether and then made weak acidic with 5 N hydrochloric acid. The aqueous layer was extracted with a THF-ethyl acetate mixed solvent, and then the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain the title compound (19 mg).

Workup

  1. customThe excess of methanol was evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. washThe aqueous layer was washed with ether
  4. extractionThe aqueous layer was extracted with a THF-ethyl acetate mixed solvent
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-78f88b96495d4cc28728f79313a37280
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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