Water → N-[2-(N-methoxyimino)propyl]phthalimide

HRID 248761Notes

Reaction equation

HRID 248761 reaction equation
O=[C:2]([CH3:15])[CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].Cl.[CH3:17][O:18][NH2:19].[OH-].[Na+].O>C(O)C>[CH3:17][O:18][N:19]=[C:2]([CH3:15])[CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 235046PhthalimidoacetoneHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 85669803N-[2-(N-methoxyimino)propyl]phthalimideYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.33 g (6.55 mmol) of N-(2-oxopropyl)phthalimide was dissolved in 30 ml of ethanol and to the solution was added 1.64 g (19.7 mmol) of O-methylhydroxylamine hydrochloride. To this suspension was added 20 ml of 2N aqueous sodium hydroxide solution, followed by being stirred at room temperature for 12 hours. The reaction mixture was poured into 100 ml of water and extracted with chloroform (30 ml×3), and the combined organic layer was dried over magnesium sulfate. Chloroform was distilled off and the residual solids were washed with hexane to give 1.03 g (yield 68%) of the titled compound as colorless crystals.

Workup

  1. extractionextracted with chloroform (30 ml×3)
  2. dry with materialthe combined organic layer was dried over magnesium sulfate
  3. distillationChloroform was distilled off
  4. washthe residual solids were washed with hexane

Sources & evidence

ORD record
ord-e09832cc5cbc41048c751f3b3abf297a
Source dataset
uspto-grants-1993_05
Patent number
US05211738

Reaction notes

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