Hydrochloric Acid → 1-Pyridin-2-yl-cyclopentanecarboxylic acid

HRID 2169461Notes

Reaction equation

HRID 2169461 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1C1(C#N)CCCC1.Cl.[C:15]([O:18]CC)(=[O:17])[CH3:16].[CH3:21][CH2:22][CH2:23][CH2:24]CC>>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:16]1([C:15]([OH:18])=[O:17])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 21226206Ethyl acetate hexaneHCID 529881341-(Pyridin-2-yl)cyclopentanecarbonitrile

Product 1

HCID 690708191-Pyridin-2-yl-cyclopentanecarboxylic acidYield 94%

Conditions

Temperature
90 °C

Procedure

In a sealed tube 1-pyridin-2-yl-cyclopentanecarbonitrile (3) (10 g, 58.14 mmol) and HCl (12N; 70 mL) were added at room temperature and the reaction mixture was stirred at 90° C. for 16 h while silica thin layer chromatography was performed (20% ethyl acetate/Hexane; Rf=0.1). The reaction mixture was concentrated; an azeotropically distilled with toluene and the residue was triturated with ether to get 1-pyridin-2-yl-cyclopentanecarboxylic acid (431) (10.5 g, 94%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. distillationan azeotropically distilled with toluene
  3. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-11ccdd1bf67a4b0c8edac486d9c076b6
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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