Sodium Hydroxide → 2-[3-(Hydroxyimino)butyl]-1H-isoindole-1,3(2H)-dione

HRID 248763

Reaktionsgleichung

Reaktionsgleichung von HRID 248763
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.[NH2:18][OH:19].[OH-].[Na+].C(=O)([O-])O.[Na+]>CO>[OH:19][N:18]=[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]

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 2907282-(3-Oxobutyl)isoindoline-1,3-dioneHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 714040032-[3-(Hydroxyimino)butyl]-1H-isoindole-1,3(2H)-dioneAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1.08 g (5.00 mmol) of N-(3-oxobutyl)phthalimide was dissolved in 10 ml of methanol and to the solution was added 0.695 g (10.0 mmol) of hydroxylamine 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 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 0.98 g (yield 84%) of the titled compound as colorless crystals.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f0c45504eaf34f9caf46112495a7d00c
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05211738

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