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

HRID 1896258Notes

Reaction equation

HRID 1896258 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 conc. 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-357a22096d7b4841b86703cb1b89a018
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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