Hydrochloric Acid → 2-Methyl-3-(pyridin-4-YL)propanoic acid

HRID 18387Notes

Reaction equation

HRID 18387 reaction equation
Cl.[CH3:2][C:3]([CH2:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)(C(OCC)=O)[C:4]([O:6]CC)=[O:5]>>[CH3:2][CH:3]([CH2:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[C:4]([OH:6])=[O:5]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 12136633Diethyl 2-methyl-2-(4-pyridylmethyl)malonate

Product 1

HCID 121366342-Methyl-3-(pyridin-4-YL)propanoic acidYield 100.3%

Procedure

Next, 6 N hydrochloric acid (96.8 ml, 581 mmol) was added to diethyl 2-methyl-2-(4-pyridylmethyl)malonate (17.2 g, 64.6 mmol), and the mixture was refluxed overnight. The reaction mixture was allowed to stand, then washed with hexane (100 ml) to remove sodium hydride oil contained in diethyl 2-methyl-2-(4-pyridylmethyl)malonate and concentrated under reduced pressure. The resulting crystals were filtered off with ethyl acetate to give 2-methyl-3-(4-pyridyl)propionic acid (10.7 g, 82%) as pale pink crystals.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. washwashed with hexane (100 ml)
  3. customto remove sodium hydride oil
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe resulting crystals were filtered off with ethyl acetate

Sources & evidence

ORD record
ord-6b9dd1b1efa3448795858f85c185548d
Source dataset
uspto-grants-2010_06
Patent number
US07741346B2

Reaction notes

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