Hydroxyamine hydrochloride → 468068-31-7

HRID 2415760Notes

Reaction equation

HRID 2415760 reaction equation
Cl.[NH2:2][OH:3].[Na].[C:5]([C:7]1[CH:12]=[CH:11][N:10]=[C:9]([N:13]([CH3:15])[CH3:14])[CH:8]=1)#[N:6]>CO>[CH3:14][N:13]([CH3:15])[C:9]1[CH:8]=[C:7]([C:5](=[N:2][OH:3])[NH2:6])[CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 5360545Sodium2×HCID 131452572-(Dimethylamino)pyridine-4-carbonitrile

Product 1

HCID 135741750468068-31-7Yield 134.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of hydroxylamine hydrochloride (0.47 g, 7.0 mmol) in methanol (10 mL) was added sodium metal (0.16 g, 7.0 mmol) portionwise. After all the sodium metal had dissolved 4-cyano-2-dimethylaminopyridine (1.0 g, 7.0 mmol) was added and the reaction was heated to reflux for 4 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 (1.7 g), which was contaminated with ethanol.

Workup

  1. additionwas added
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 4 hours
  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-bcfad0b031824868932357910f929a60
Source dataset
uspto-grants-2004_11
Patent number
US06821972B2

Reaction notes

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