Sodium Hydroxide → (RS)-phenyl-pyridin-2-yl-acetic acid methyl ester

HRID 1266238Notes

Reaction equation

HRID 1266238 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[C:8](N)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:17].[Na+].Cl.[CH3:20]O>>[CH3:20][O:9][C:8](=[O:17])[CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 97964alpha-Phenyl-2-pyridineacetamideHCID 21893726Hydrochloride methanol

Product 1

HCID 3346835(RS)-phenyl-pyridin-2-yl-acetic acid methyl esterYield 59%

Procedure

(RS)-Phenyl-pyridin-2-yl-acetamide (0.340 g, 1.60 mmol) was dissolved in 5 ml of a saturated solution of HCl/methanol and refluxed for 6 h in a closed vessel. The mixture is poured on 25 g of ice, the pH is adjusted to 8-9 by cautious addition of 28% sodium hydroxide solution keeping the temperature below 10° C. and the product is extracted with ethyl acetate/water. After drying (MgSO4) and concentration, the crude material is purified by flash chromatography on silicagel using 1:4 mixture of ethyl acetate and hexane as eluant to yield 0.204 g (0.939 mmol, 59%) of (RS)-phenyl-pyridin-2-yl-acetic acid methyl ester as a white solid, m.p. 74° C. and MS: m/e=228.2 (M+H+).

Workup

  1. temperaturerefluxed for 6 h in a closed vessel
  2. customthe temperature below 10° C.
  3. extractionthe product is extracted with ethyl acetate/water
  4. customAfter drying
  5. concentration(MgSO4) and concentration
  6. customthe crude material is purified by flash chromatography on silicagel
  7. addition1:4 mixture of ethyl acetate and hexane as eluant

Sources & evidence

ORD record
ord-e259f6bfebd7403885b51c9a026f4b53
Source dataset
uspto-grants-2003_04
Patent number
US06548522B1

Reaction notes

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