5-Chloronaproxen, (S)- → Naproxen

HRID 3976

Reaction equation

HRID 3976 reaction equation
Cl[C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C@H:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:7]2>[OH-].[Na+].[Al].[Ni]>[CH3:13][O:12][C:11]1[CH:2]=[C:3]2[C:8](=[CH:9][CH:10]=1)[CH:7]=[C:6]([C@H:14]([CH3:18])[C:15]([OH:17])=[O:16])[CH:5]=[CH:4]2

Participants

4

Reactant 1

HCID 130752095-Chloronaproxen, (S)-

Product 1

HCID 156391Naproxen

Reagents, catalysts & solvents 2

HCID 6336846Nickel aluminideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1 g of (S)-2-(5-chloro-6-methoxy-2-naphthyl)-propionic acid in 20 ml of 10% aqueous sodium hydroxide solution at 90° C. is treated with 3 g of a nickel-aluminum alloy in small portions. After stirring the mixture for two hours, it is filtered, diluted with excess dilute hydrochloric acid and extracted with methylene chloride. The organic phase is evaporated to dryness and the residue recrystallized from methylene chloride/hexane to yield (S)-2-(6-methoxy-2-naphthyl)propionic acid after recrystallization.

Workup

  1. filtrationit is filtered
  2. additiondiluted with excess dilute hydrochloric acid
  3. extractionextracted with methylene chloride
  4. customThe organic phase is evaporated to dryness
  5. customthe residue recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-0089af8057e946a18b16755f3f9439f0
Source dataset
uspto-grants-1988_02
Patent number
US04723033

Linked notes

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