Réaction #1026

Équation de réaction

1-acetyl-isoquinoline

hydroxylamine

sodium acetate

methanol

→

1-acetyl-isoquinoline oxime

Rendement 58.0%

Solvants

water

water

Conditions de réaction

Traitement

1. 1
   Températureto reflux for 8 hours
2. 2
   Extractionextracted with ethyl acetate
3. 3
   AutreThe combined extracts were dried
4. 4
   Concentrationconcentrated
5. 5
   Autrechromatographed

Mode opératoire

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.

Source