Sodium Bicarbonate → 2-Methyl-3-(pyridin-4-YL)propanoic acid

HRID 2176894Notes

Reaction equation

HRID 2176894 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH:8](C(C(OCC)=O)C(OCC)=O)[CH3:9])=[CH:3][CH:2]=1.[C:21](=[O:24])(O)[O-:22].[Na+]>Cl>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH:8]([CH3:9])[C:21]([OH:22])=[O:24])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67382816HCID 67382816, compound

Product 1

HCID 121366342-Methyl-3-(pyridin-4-YL)propanoic acidYield 76.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Compound diethyl 2-(1-(pyridin-4-yl)propan-2-yl)malonate (2.50 g, 9.43 mmol) was refluxed in cone. HCl (30 ml) for 16 h. The pH of the reaction mixture was adjusted to 6 by adding solid sodium bicarbonate and extracted with ethyl acetate. The combined ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to afford 1.20 g (76.9%) of 2-((pyridin-4-yl)methyl)propanoic acid as an off-white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined ethyl acetate layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-6064429c0a954da8bc54095bd283aade
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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