Sodium Hydroxide → HCID 9880243, compound

HRID 2216846Notes

Reaction equation

HRID 2216846 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[C:16]([C:18]([O:20]C)=[O:19])[CH:15]=[C:14]([O:22][CH2:23][CH:24]=[CH2:25])[CH:13]=2)[O:9][N:8]=1.[OH-].[Na+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[C:16]([C:18]([OH:20])=[O:19])[CH:15]=[C:14]([O:22][CH2:23][CH:24]=[CH2:25])[CH:13]=2)[O:9][N:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9902359HCID 9902359, compound

Product 1

HCID 9880243HCID 9880243, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred suspension of 3-(2-pyridyl)-5-(3-alloxy-5-(methoxycarbonyl)phenyl)-1,2,4-oxadiazole (160 mg, 0.47 mmol) in methanol (5 mL) at ambient temperature was treated with 1 M sodium hydroxide (0.8 mL, 0.80 mmol). The reaction was stirred 16 hours and solvent was removed in vacuo. The residue was dissolved in a small amount of water and then acidified with 1 N hydrogen chloride. Extraction of the aqueous phase with dichloromethane followed by concentration in vacuo afforded 104.5 mg of 3-(2-pyridyl)-5-(3-alloxy-5-(hydroxycarbonyl)phenyl)-1,2,4-oxadiazole.

Workup

  1. customsolvent was removed in vacuo
  2. dissolutionThe residue was dissolved in a small amount of water
  3. extractionExtraction of the aqueous phase with dichloromethane
  4. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-e4fc9643d89f4f9a8914f4bda2d8e58b
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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