Hydrochloric Acid → 2-[4-(2-Hydroxyiminocyclopentan-1-ylmethyl)phenyl]propionic Acid

HRID 971867Notes

Reaction equation

HRID 971867 reaction equation
O=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1.Cl.[NH2:20][OH:21].[OH-].[Na+].Cl>C(O)C.O>[OH:21][N:20]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3965LoxoprofenHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 737697752-[4-(2-Hydroxyiminocyclopentan-1-ylmethyl)phenyl]propionic AcidYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 1.5 g of 2-[4-(2-oxocyclopentan-1-ylmethyl)phenyl]propionic acid in 10 ml of ethanol was added a solution of 0.43 g of hydroxylamine hydrochloride in 2 ml of water, subsequently a solution of 0.76 g of sodium hydroxide in 2 ml of water, and the mixture was heated under reflux for 3 hours. The reaction mixture was poured into an ice-water, acidified by addition of hydrochloric acid, and then extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent removed by distillation to give 1.4 g of crystals of the desired compound. Recrystallization of the product from a mixture of ether-n-hexane afforded colorless crystals, m.p. 146°-148° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent removed by distillation

Sources & evidence

ORD record
ord-bc86232e2e744752901580f5a07f2169
Source dataset
uspto-grants-1979_07
Patent number
US04161538

Reaction notes

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