3-Cyanopyridine → N-Hydroxynicotinimidamide

HRID 475533Notes

Reaction equation

HRID 475533 reaction equation
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[Na+].[Na+].[C:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)#[N:11].O>CO>[OH:3][N:2]=[C:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[NH2:11]

Participants

6

Reactant 4

HCID 793-CyanopyridineHCID 962WaterHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 308113N-Hydroxynicotinimidamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

Hydroxylamine hydrochloride (1.3 g) and sodium carbonate (2.0 g) were added to a mixed solution of 3-cyanopyridine in methanol (10 ml)/water (10 ml) and the mixture was stirred at 100° C. for 2.5 hours. After distilling off the solvent under reduced pressure, water was added to the residue and extracted with tetrahydrofuran, and the organic layer was washed with saturated brine. The organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure to obtain N′-hydroxypyridine-3-carboximidamide (1.3 g) as a colorless oily substance.

Workup

  1. distillationAfter distilling off the solvent under reduced pressure, water
  2. additionwas added to the residue
  3. extractionextracted with tetrahydrofuran
  4. washthe organic layer was washed with saturated brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6b8aff50edd948fd96ba14cd6b810db4
Source dataset
uspto-grants-2014_01
Patent number
US08637557B2

Reaction notes

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