Pyridine → 1-(4-Chlorophenyl)-1-propanone oxime

HRID 2264041Notes

Reaction equation

HRID 2264041 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH3:10])=[CH:4][CH:3]=1.Cl.[NH2:13][OH:14].N1C=CC=CC=1>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:13][OH:14])[CH2:9][CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 226974'-ChloropropiophenoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 740541671-(4-Chlorophenyl)-1-propanone oximeYield 54.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-Chlorophenyl)propan-1-one (8.4 g, 50 mmol) was combined with hydroxylamine hydrochloride (4.0 g, 58 mmol), pyridine (4.6 g, 58 mmol), and ethanol (75 mL). The mixture was refluxed for 3 h. Solvent was evaporated and the residue diluted with water and extracted into diethyl ether/hexane (1:1). The organic extracts were washed with water, brine, and dried over anhydrous magnesium sulfate. Crystallization from cold hexane gave 5.0 g of 1-(4-chlorophenyl)propan-1-one oxime.

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. customSolvent was evaporated
  3. additionthe residue diluted with water
  4. extractionextracted into diethyl ether/hexane (1:1)
  5. washThe organic extracts were washed with water, brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customCrystallization from cold hexane

Sources & evidence

ORD record
ord-4b6730e5952a4456bd373186fadb2a21
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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