Hydroxyamine hydrochloride → Ethanone, 1-(6-fluoro-3-pyridinyl)-, oxime

HRID 75960Notes

Reaction equation

HRID 75960 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.Cl.[NH2:12][OH:13].CC([O-])=O.[Na+]>O.CCO>[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[N:12][OH:13])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 130903391-(6-Fluoropyridin-3-yl)ethan-1-one

Product 1

HCID 86620627Ethanone, 1-(6-fluoro-3-pyridinyl)-, oxime

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a 200-ml, round bottom flask was added, 1-(6-fluoropyridin-3-yl)ethanone (Method 65, 2.5 g, 17.9 mmol), hydroxylamine hydrochloride (2.5 g, 35.8 mmol), and NaOAc (3.7 g, 44.8 mmol) in a solution of water-EtOH (65 ml, 3.3:1). The resulting mixture was heated to 50° C. for 1 hour. The reaction was then allowed to cool to room temperature, partitioned with EtOAc, layers were cut, and organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to afford the title compound in quantitative yield. 1H NMR: 11.49 (s, 1H) 8.47 (s, 1H) 8.17-8.27 (m, 1H) 7.21 (dd, J=8.29, 3.01 Hz, 1H) 2.17 (s, 3H).

Workup

  1. additionTo a 200-ml, round bottom flask was added
  2. temperatureto cool to room temperature
  3. custompartitioned with EtOAc, layers
  4. dry with materialorganic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4fe2b9f4f93b454fb72cb30e65a15f56
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Reaction notes

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