Sodium Carbonate → 2',4'-Dichloro-2-(3-pyridyl)acetophenone O-isobutyloxime

HRID 1681304Notes

Reaction equation

HRID 1681304 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl.[CH2:25]([O:29][NH2:30])[CH:26]([CH3:28])[CH3:27]>C(O)C>[CH2:25]([O:29][N:30]=[C:9]([C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH:26]([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 12696238O-(2-Methylpropyl)hydroxylamine--hydrogen chloride (1/1)HCID 13488634Ethanone, 1-(2,4-dichlorophenyl)-2-(3-pyridinyl)-

Product 1

HCID 542106562',4'-Dichloro-2-(3-pyridyl)acetophenone O-isobutyloxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4.65 g of 2',4'-dichloro-2-(3-pyridyl)acetophenone in 25 ml of ethanol is treated with 2.70 g of anhydrous sodium carbonate and 2.63 g of O-isobutylhydroxylamine hydrochloride and the reaction mixture is then heated to reflux temperature with stirring. After 4 hours, it is poured onto ice and extracted with ethyl acetate. The organic phase is washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. 2',4'-Dichloro-2-(3-pyridyl)acetophenone O-isobutyloxime is obtained as an E/Z isomer mixture in the form of a brownish oil. In the chromatographic separation on silica gel using n-hexane/ethyl acetate (7:3), the E isomer [1H-NMR (CDCl3, 200 MHz): 2.055 ppm (heptet, HC(CH3)2)] is eluted first and then the Z isomer [1H-NMR (CDCl3, 200 MHz): 1.928 ppm (heptet, HC(CH3)2)].

Workup

  1. temperaturethe reaction mixture is then heated
  2. temperatureto reflux temperature
  3. additionit is poured onto ice
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-52b947c0985048b2a72489a78832222e
Source dataset
uspto-grants-1992_12
Patent number
US05171354

Reaction notes

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