Hydroxyamine hydrochloride → 5-Bromo-4-methyl-pyridine-2-carbaldehyde oxime

HRID 1027594Notes

Reaction equation

HRID 1027594 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5]([CH:8]=O)=[N:6][CH:7]=1.Cl.[NH2:12][OH:13].C([O-])(=O)C.[Na+]>CCO.O>[Br:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5]([CH:8]=[N:12][OH:13])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 594745005-Bromo-4-methylpicolinaldehyde

Product 1

HCID 1363413885-Bromo-4-methyl-pyridine-2-carbaldehyde oximeYield 66%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of the compound obtained in Step B (3.1 g) in EtOH (47.5 ml) and water (23 ml) were added hydroxylamine hydrochloride (1.4 g) and sodium acetate (1.9 g). The reaction was stirred for 15 min at room temperature. The white solid was filtered off and the solution concentrated in vacuo to afford the crude title product (2.2 g, white solid), which was used directly for the next step. LCMS (Method F) 2.09 min, M+H 564/566.

Workup

  1. filtrationThe white solid was filtered off
  2. concentrationthe solution concentrated in vacuo

Sources & evidence

ORD record
ord-81b2912c0bab483b8928743b60cccea6
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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