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

HRID 1725843Notes

Reaction equation

HRID 1725843 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 10.7 g (82%) of 2-methyl-3-(4-pyridyl)propionic acid 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-8bfe7e33145d47d281166539c5ea2a8d
Source dataset
uspto-grants-2009_02
Patent number
US07491739B2

Reaction notes

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