Hydroxyamine hydrochloride → HCID 73430681, compound

HRID 1517595Notes

Reaction equation

HRID 1517595 reaction equation
[Br:1][C:2]1[C:7]([CH:8]=O)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[NH2:11][OH:12].C([O-])(=O)C.[Na+]>C(O)C>[Br:1][C:2]1[C:7]([CH:8]=[N:11][OH:12])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 47149512-Bromonicotinaldehyde

Product 1

HCID 73430681HCID 73430681, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-bromopyridine-3-carbaldehyde (2.04 g) in ethanol (25 mL) is added hydroxylamine hydrochloride (948 mg, 13.16 mmol) and sodium ethanoate (1.09 g, 13.16 mmol). The mixture is stirred at room temperature overnight. The solvent is evaporated under reduced pressure and the residue partitioned between dichloromethane and water. The organic layer is separated, dried over sodium sulfate, filtered and solvent evaporated in vacuo to give 2 g of 2-bromopyridine-3-carbaldehyde oxime. MS (m/z): 201/203 (M+1/M+3)

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. customthe residue partitioned between dichloromethane and water
  3. customThe organic layer is separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customsolvent evaporated in vacuo

Sources & evidence

ORD record
ord-200f4cb1d7e644418eb0185896c11deb
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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