Hydroxyamine hydrochloride → 6-Chloro-N-hydroxy-nicotinamidine

HRID 2415761Notes

Reaction equation

HRID 2415761 reaction equation
C[O-].[Na+].Cl.[NH2:5][OH:6].[C:7]([C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[N:13][CH:14]=1)#[N:8]>CO>[Cl:15][C:12]1[N:13]=[CH:14][C:9]([C:7](=[N:5][OH:6])[NH2:8])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 336784996-Chloro-N-hydroxy-nicotinamidineYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium methoxide (15.6 g of 25-30% in methanol, 72 mmol) in methanol (70 mL) at 0° C. was added hydoxylamine hydrochloride (5.02 g, 72 mmol) and the mixture was then stirred at room temperature for 30 minutes. 5-cyano-2-chloropyridine (10 g, 72 mmol) was added and the reaction was heated to reflux for 3 hours. The reaction was cooled to room temperature, filtered to remove precipitated sodium chloride and the filtrate was evaporated to dryness. The residue was dissolved in ethanol in order to crystallise the product but this was unsuccessful, so the solvent was removed in vacuo to give the title compound as a white solid (12 g).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 3 hours
  3. temperatureThe reaction was cooled to room temperature
  4. filtrationfiltered
  5. customto remove
  6. customprecipitated sodium chloride
  7. customthe filtrate was evaporated to dryness
  8. dissolutionThe residue was dissolved in ethanol in order
  9. customto crystallise the product
  10. customthis was unsuccessful, so the solvent was removed in vacuo

Sources & evidence

ORD record
ord-1869a8da83194c13870fab7419daf62d
Source dataset
uspto-grants-2004_11
Patent number
US06821972B2

Reaction notes

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