Sodium Carbonate → 5-Bromo-2-fluoro-3-pyridinecarboxaldehyde oxime

HRID 55858

Reaction equation

HRID 55858 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=O)[C:5]([F:8])=[N:6][CH:7]=1.Cl.[NH2:12][OH:13].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[N:12][OH:13])[C:5]([F:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 454801925-Bromo-2-fluoro-3-pyridinecarboxaldehyde

Product 1

HCID 1317368795-Bromo-2-fluoro-3-pyridinecarboxaldehyde oximeYield 97.8%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of 5-bromo-2-fluoro-pyridine-3-carbaldehyde (2) (20.0 g, 98.0 mmol) in 1:1 MeOH—H2O (250 mL) was added hydroxylamine hydrochloride (7.52 g, 108 mmol) and sodium carbonate (11.4 g, 108 mmol). The reaction mixture was stirred at rt for 1 hour. The solvent was evaporated in vacuo and the residue diluted with H2O (200 mL) and EtOAc (200 mL). The organic phase was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The product was obtained as a light pink solid (21.0 g, 93%); Rf: 0.4 (10% EtOAc-pet ether).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionthe residue diluted with H2O (200 mL) and EtOAc (200 mL)
  3. customThe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-e1b82a2e6c5043789b778fa207d56113
Source dataset
uspto-grants-2016_09
Patent number
US09433622B2

Linked notes

Loading…