Sodium Hydroxide → HCID 9880243, compound

HRID 431953Notes

Reaction equation

HRID 431953 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 1M 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 1N hydrogen chloride. Extraction of the aqueous phase with dichloromethane followed by concentration in vacuo afforded 104.5mg 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-b684aa2c699343be8c22666b4698020c
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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