Reaktion #1026

Reaktionsgleichung

1-acetyl-isoquinoline

hydroxylamine

sodium acetate

methanol

→

1-acetyl-isoquinoline oxime

Ausbeute 58.0%

Lösungsmittel

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux for 8 hours
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   SonstigeThe combined extracts were dried
4. 4
   Einengenconcentrated
5. 5
   Sonstigechromatographed

Vorschrift

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.

Quelle