Sodium Hydroxide → 5-(2-Methoxyethoxy)picolinic acid

HRID 81615Notes

Reaction equation

HRID 81615 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[CH:7][N:6]=1)=[O:4].[OH-].[Na+]>C1COCC1>[CH3:15][O:14][CH2:13][CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 666655885-(2-Methoxyethoxy)pyridine-2-carboxylic acid methyl ester

Product 1

HCID 587956345-(2-Methoxyethoxy)picolinic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(2-methoxy-ethoxy)-pyridine-2-carboxylic acid methyl ester (390 mg, 0.489 mmol) in THF (3 ml) was added 1M aqueous NaOH (0.538 ml). The reaction mixture was stirred at room temperature for 2.5 h, concentrated, the residue was dissolved in EtOAc and washed twice with water. The aqueous layers were acidified with 1M aqueous HCl (0.538 ml) and the title compound was isolated by lyophilisation.

Workup

  1. concentrationconcentrated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed twice with water

Sources & evidence

ORD record
ord-79476eb836944b1f9cca20ed82b1606e
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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