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

HRID 11444Notes

Reaction equation

HRID 11444 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-f6144ee0e8f24ce288490dbd6a6d4c57
Source dataset
uspto-grants-2006_08
Patent number
US07098226B2

Reaction notes

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