Potassium Carbonate → N'-Hydroxy-3-(pyridin-3-yl)propanimidamide

HRID 1594648Notes

Reaction equation

HRID 1594648 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][C:9]#[N:10])[CH:2]=1.Cl.[NH2:12][OH:13].C([O-])([O-])=O.[K+].[K+]>C(O)C.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][C:9](=[N:12][OH:13])[NH2:10])[CH:2]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 100119303-(Pyridin-3-yl)propanenitrile

Product 1

HCID 53434814N'-Hydroxy-3-(pyridin-3-yl)propanimidamideYield 61%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

20.1 g (0.15 mol) of 3-(3-pyridyl)propionitrile is dissolved in a mixture of 61 ml of ethanol, and 15 ml of water and 9.5 g (0.14 mol) of hydroxylamine hydrochloride and 21 g (0.15 mol) of K2CO3 are added. After 24 hours at reflux, the solvent is removed in a vacuum, and the residue is extracted twice with ethanol. The extracts are concentrated by evaporation and recrystallized in hot ethanol. 14.1 g (56%) of product is obtained. Melting point 119-121° C.

Workup

  1. additionare added
  2. temperatureAfter 24 hours at reflux
  3. customthe solvent is removed in a vacuum
  4. extractionthe residue is extracted twice with ethanol
  5. concentrationThe extracts are concentrated by evaporation
  6. customrecrystallized in hot ethanol

Sources & evidence

ORD record
ord-b393dc8caa744229825b536b32bbf8e9
Source dataset
uspto-grants-2001_09
Patent number
US06284779B1

Reaction notes

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