Sodium Hydroxide → N-[3-(N-methoxyimino)butyl]phthalimide

HRID 248765

Reaction equation

HRID 248765 reaction equation
O=[C:2]([CH3:16])[CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].Cl.[CH3:18][O:19][NH2:20].[OH-].[Na+].C(=O)([O-])O.[Na+]>CO>[CH3:18][O:19][N:20]=[C:2]([CH3:16])[CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 2907282-(3-Oxobutyl)isoindoline-1,3-dioneHCID 516892Sodium BicarbonateHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 73653096N-[3-(N-methoxyimino)butyl]phthalimideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.08 g (5.00 mmol) of N-(3-oxobutyl)phthalimide was dissolved in 10 ml of methanol and to the solution was added 0.835 g (10.0 mmol) of O-methylhydroxylamine hydrochloride. To this suspension was added 2 ml of 5N aqueous sodium hydroxide solution, followed by being stirred at room temperature for 16 hours. The reaction mixture was poured into 100 ml of saturated aqueous sodium hydrogencarbonate solution 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 1.23 g (yield 100%) of the titled compound as white 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-78a5f493192c43bc976d6ca3062ec675
Source dataset
uspto-grants-1993_05
Patent number
US05211738

Linked notes

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