Water → HCID 178510887, compound

HRID 873312Notes

Reaction equation

HRID 873312 reaction equation
Cl.[NH2:2][OH:3].O.C([O-])(O)=O.[Na+].[Br:10][C:11]1[C:12]([CH2:17][C:18]#[N:19])=[N:13][CH:14]=[CH:15][CH:16]=1>C(O)C>[Br:10][C:11]1[C:12]([CH2:17][C:18]([NH:2][OH:3])=[NH:19])=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 6428252-(3-Bromopyridin-2-yl)acetonitrile2×

Product 1

HCID 178510887HCID 178510887, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A vigorously stirred mixture of hydroxylamine hydrochloride (924 mg, 13.3 mmol), water (4 mL), NaHCO3 (1.12 g, 13.3 mmol), 3-bromo-2-cyanomethylpyridine (Intermediate 1) (1.31 g, 6.65 mmol) and ethanol (14 mL) was heated to reflux for 5 h. The reaction mixture was allowed to cool to room temperature, the ethanol was removed in vacuo and the white solid collected by filtration, washing with water (3×10 mL). The wet solid was dried in vacuo at 40° C. for 1 h to yield 2-(3-Bromo-pyridin-2-yl)-N-hydroxy-acetamidine as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 h
  3. customthe ethanol was removed in vacuo
  4. filtrationthe white solid collected by filtration
  5. washwashing with water (3×10 mL)
  6. customThe wet solid was dried in vacuo at 40° C. for 1 h

Sources & evidence

ORD record
ord-20132b91e54b47b1a1584c1e01b17469
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

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