Hydroxylamine → 1-Acetyl-isoquinoline oxime

HRID 930

Reaktionsgleichung

Reaktionsgleichung von HRID 930
[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][N:5]=1)(=O)[CH3:2].[NH2:14][OH:15].C([O-])(=O)C.[Na+].CO>O>[C:1](=[N:14][OH:15])([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][N:5]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 787HydroxylamineHCID 887MethanolHCID 517045Sodium AcetateHCID 131572141-(Isoquinolin-1-yl)ethan-1-one

Produkt 1

HCID 6392871-Acetyl-isoquinoline oximeAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of 1-acetyl-isoquinoline (3.42 g), hydroxylamine (1.53 g) and sodium acetate (2.46 g) in a 3:1 mixture of methanol:water (80 ml) was heated to reflux for 8 hours then allowed to stand for 16 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The combined extracts were dried, concentrated and chromatographed using ethyl acetate:hexane 3:7 as the eluant to give 1-acetyl-isoquinoline oxime (1.87 g, 58% yield) as a white crystalline solid m.p. 154.4°-155.3° C.; 1H NMR: 2.50(3H,s); 7.58-7.73(3H,m); 7.85(1H,m); 8.55(1H,m); 8.57(1H,m); 8.66(1H,s) ppm.

Aufarbeitung

  1. temperatureto reflux for 8 hours
  2. extractionextracted with ethyl acetate
  3. customThe combined extracts were dried
  4. concentrationconcentrated
  5. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-1c93b7108442465f805b25dd4eb5e4ed
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723473

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