Hydrochloric Acid → 6-Methoxy-3-pyridineacetic acid

HRID 747865

Reaction equation

HRID 747865 reaction equation
C([O:3][C:4](=[O:19])[CH:5]([C:11]1[CH:12]=[N:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)C(OCC)=O)C.O.Cl.[OH-].[Na+]>[OH-].[Na+].C1COCC1>[CH3:18][O:17][C:14]1[N:13]=[CH:12][C:11]([CH2:5][C:4]([OH:19])=[O:3])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 59750617HCID 59750617, compound

Product 1

HCID 119534926-Methoxy-3-pyridineacetic acid

Reagents, catalysts & solvents 1

HCID 20445995Sodium hydroxide tetrahydrofuranSolvent

Procedure

2-(6-Methoxy-pyridin-3-yl)-malonic acid diethyl ester (5.6 g, 21.0 mmoL) prepared in Example 3 was dissolved in 2N NaOH/THF:H2O (1:1) (20 mL). The resulting mixture was heated to reflux for 3 hours. The reaction mixture was then adjusted to pH=1 by concentrated HCl and stirred at room temperature for another 1 hour. The solution was then adjusted to pH=13 by 1N NaOH and extracted with ether. The aqueous phase was acidified to pH=5 by 1N HCl and extracted 3× by ethyl acetate. The combined organic phase was then washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the title compound a white solid (2.45, 70%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 3 hours
  3. extractionextracted with ether
  4. extractionextracted 3× by ethyl acetate
  5. washThe combined organic phase was then washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d0fdc75ef94e4a17bdaafe818acaffdb
Source dataset
uspto-grants-2008_07
Patent number
US07399767B2

Linked notes

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