Hydroxyamine hydrochloride → N-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]phthalimide

HRID 55985Notes

Reaction equation

HRID 55985 reaction equation
[Cl:1][C:2]1[C:3]([C:9](=O)[CH2:10][N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.[NH2:24][OH:25]>C(O)C>[Cl:1][C:2]1[C:3]([C:9](=[N:24][OH:25])[CH2:10][N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 118071534N-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]phthalimide

Product 1

HCID 136987064N-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]phthalimideYield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 0.32 g of N-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]phthalimide in 15 ml of ethanol, 0.66 g of hydroxylamine hydrochloride was added and refluxed with heating for 4 hours with stirring. After completion of the reaction, the solvent was evaporated under reduced pressure, and the reaction mixture was mixed with 30 ml of water and 50 ml of ethyl acetate, and the resulting organic layer was collected. The organic layer was washed with water (30 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the resulting residue was washed with 10 ml of hexane to obtain 265 mg of the desired product as yellow crystals.

Workup

  1. temperaturerefluxed
  2. temperaturewith heating for 4 hours
  3. customAfter completion of the reaction
  4. customthe solvent was evaporated under reduced pressure
  5. additionthe reaction mixture was mixed with 30 ml of water and 50 ml of ethyl acetate
  6. customthe resulting organic layer was collected
  7. washThe organic layer was washed with water (30 ml×1)
  8. dry with materialdried over saturated aqueous sodium chloride
  9. customanhydrous sodium sulfate, the solvent was evaporated under reduced pressure
  10. washthe resulting residue was washed with 10 ml of hexane

Sources & evidence

ORD record
ord-6bbf5079bed94fd286080e1a7dbb8825
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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