Hydroxylamine → 3-Acetyl-isoquinoline oxime

HRID 932

Reaktionsgleichung

Reaktionsgleichung von HRID 932
[C:1]([C:4]1[N:5]=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)(=O)[CH3:2].[NH2:14][OH:15].C([O-])(=O)C.[Na+]>CO.O>[C:1](=[N:14][OH:15])([C:4]1[N:5]=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:2]

Komponenten

6

Edukt 3

HCID 787HydroxylamineHCID 517045Sodium AcetateHCID 112752751-(Isoquinolin-3-yl)ethan-1-one

Produkt 1

HCID 1363959913-Acetyl-isoquinoline oximeAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of 3-acetyl-isoquinoline (0.65 g), hydroxylamine (0.29 g) and sodium acetate (0.47 g) in a mixture of methanol (20 ml) and water (3 ml) was heated to reflux for 1.5 hours. The reaction was then poured into water and extracted with ethyl acetate. The combined extracts were dried, concentrated and triturated with hexane to give 3-acetyl-isoquinoline oxime (0.63, 89% yield) as a white crystalline solid m.p. 135°-142° C.; 1H NMR: 2.50(3H,s); 7.61(1H,t); 7.70(1H,t); 7.87(1H,d); 7.99(1H,d); 8.11(1H,s); 9.28(1H,s) ppm.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 hours
  3. extractionextracted with ethyl acetate
  4. customThe combined extracts were dried
  5. concentrationconcentrated
  6. customtriturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-6886621a94c642309e84fee2699ce813
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723473

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