Sulfuric Acid → 3-(Pyridin-4-yl)propanoic acid

HRID 1822187

Reaction equation

HRID 1822187 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([O:11]CC)=[O:10])=[CH:3][CH:2]=1.S(=O)(=O)(O)O>[OH-].[Na+]>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 12229233Ethyl isonicotinylacetate

Product 1

HCID 2332433-(Pyridin-4-yl)propanoic acidYield 70%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of ethyl 3-(pyridin-4-yl)propionate (17.14 g, 96 mmol; synthesized according to WO, A, 01/42244) in aqueous sodium hydroxide (2N, 100 ml) was heated under reflux for 1 hour, cooled, then adjusted pH 4 to 5 with conc. sulfuric acid, filtered to give precipitates which were washed with water, and then with hexane, and dried to afford 3-(pyridin-4-yl)propionic acid (10.15 g, 70%) as crystals.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperaturecooled
  3. filtrationfiltered
  4. customto give
  5. customprecipitates which
  6. washwere washed with water
  7. dry with materialwith hexane, and dried

Sources & evidence

ORD record
ord-97dab19923534c1195d444cc8b61ce7a
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Linked notes

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