Sodium Hydroxide → (4-Methylpyridin-2-yl)acetic acid

HRID 2245340Notes

Reaction equation

HRID 2245340 reaction equation
C([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][N:7]=1)C.[OH-].[Na+]>C(O)C>[CH3:12][C:10]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:5][C:4]([OH:13])=[O:3])[CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13400650HCID 13400650, compound

Product 1

HCID 19380987(4-Methylpyridin-2-yl)acetic acidYield 118.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(4-Methyl-pyridin-2-yl)-acetic acid ethyl ester (1.0 g)—prepared according to Chem. Parm. Bull 32 (12), 1984, 4866-4872—was dissolved in ethanol (30 ml) and treated with a 1M ethanolic NaOH solution (5.83 ml). The mixture was refluxed for 4 hours, cooled and evaporated in vacuo. The residue was dissolved in water (50 ml) and the pH was adjusted to 3.0 with 1M HCl. The solvent was evaporated and the residue was suspended in ethanol (150 ml) and filtered. The clear filtrate was evaporated to dryness and the residue was dried in vacuo to give a light yellow solid (1.0 g). NMR (DMSO-d6): 8.65 (d, 1H); 7.72 (s, 1H), 7.68 (d, 1H), 4.04 (s, 2H), 2.49 (s, 3H).

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. temperaturecooled
  3. customevaporated in vacuo
  4. dissolutionThe residue was dissolved in water (50 ml)
  5. customThe solvent was evaporated
  6. filtrationfiltered
  7. customThe clear filtrate was evaporated to dryness
  8. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-af3eeaf8d99d49dc99edff22ce0b2c98
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

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