3-Pyridinecarboxaldehyde → 3-Pyridine aldoxime

HRID 2232090Notes

Reaction equation

HRID 2232090 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.Cl.[NH2:10][OH:11].C([O-])(O)=O.[Na+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[N:10][OH:11])[CH:2]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 6943-Pyridine aldoximeYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Pyridine carboxaldehyde (21.4 g, 200 mmol) and hydroxylamine hydrochloride (14.6 g, 210 mmol) were dissolved in CH3OH (125 ml) and heated at reflux for 12 hours. The solution was then concentrated under vacuum to give a white solid. To this solid was added saturated NaHCO3 solution, with stirring until slightly basic. A white precipitate was obtained which was filtered, washed with water, and dried in vacuo, to give 3-pyridine aldoxime as a white solid, 23.6 g, 97% yield, mp 148°-150° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 12 hours
  3. concentrationThe solution was then concentrated under vacuum
  4. customto give a white solid
  5. customA white precipitate was obtained which
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-be88b38d759546368fe742f49397be5c
Source dataset
uspto-grants-1988_11
Patent number
US04786648

Reaction notes

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