Tert-Butyl nitrite → 2-(Hydroxyimino)-1-phenyl-2-(pyridin-3-yl)ethanone

HRID 1430602Notes

Reaction equation

HRID 1430602 reaction equation
[C:1]1([C:7](=[O:15])[CH2:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:16](OC(C)(C)C)=[O:17].[O-]CC.[Na+]>CCO.O>[OH:17][N:16]=[C:8]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:15]

Participants

6

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 2383351-Phenyl-2-(pyridin-3-yl)ethanoneHCID 2723922Sodium ethoxide

Product 1

HCID 858094212-(Hydroxyimino)-1-phenyl-2-(pyridin-3-yl)ethanoneYield 37.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-phenyl-2-(pyridine-3-yl)ethanone (0.494 g, 2.505 mmol) in EtOH (36.8 mL) at room temperature was added tert-butyl nitrite (0.586 mL, 4.93 mmol) dropwise followed by sodium ethoxide (0.435 g, 2.55 mmol). The reaction was stirred at room temperature overnight. Upon completion, the solvent was evaporated to give a yellow oil. This oil was then diluted with H2O (25 mL), extracted with EtOAc (3×50 mL), dried over MgSO4, filtered and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a yellow solid (0.214 g). LCMS m/z=227.4 [M+H]+.

Workup

  1. customUpon completion, the solvent was evaporated
  2. customto give a yellow oil
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0629d7913cc2491a9ac8c7dac427627e
Source dataset
uspto-grants-2015_01
Patent number
US08940891B2

Reaction notes

Loading…