Hydroxylamine → 1-[4-(4-Chloro-2-fluoro-phenoxy)-phenyl]-ethanone-oxime

HRID 1406332Notes

Reaction equation

HRID 1406332 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13](=O)[CH3:14])=[CH:9][CH:8]=2)=[C:4]([F:18])[CH:3]=1.[NH2:19][OH:20]>C(O)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13](=[N:19][OH:20])[CH3:14])=[CH:9][CH:8]=2)=[C:4]([F:18])[CH:3]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 667903211-(4-(4-Chloro-2-fluorophenoxy)phenyl)ethanone

Product 1

HCID 866588121-[4-(4-Chloro-2-fluoro-phenoxy)-phenyl]-ethanone-oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.4 g (12.8 mmol) of 1-[4-(4-chloro-2-fluoro-phenoxy)-phenyl]-ethanone and 3.0 mL hydroxylamine solution (50% in water) in 100 mL ethanol was refluxed for five hours. Then the mixture was evaporated to dryness, the residue was combined with approx. 15 mL water and extracted three times with 10 mL ethyl acetate. The extracts were washed with saturated sodium chloride solution, dried and evaporated down. The product thus obtained was reacted further without any further purification.

Workup

  1. temperaturewas refluxed for five hours
  2. customThen the mixture was evaporated to dryness
  3. extractionextracted three times with 10 mL ethyl acetate
  4. washThe extracts were washed with saturated sodium chloride solution
  5. customdried
  6. customevaporated down
  7. customThe product thus obtained
  8. customwas reacted further without any further purification

Sources & evidence

ORD record
ord-e4b5dc36bc5c41c088d3f3b12c768717
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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