Reacción #1026

Ecuación de reacción

1-acetyl-isoquinoline

hydroxylamine

sodium acetate

methanol

→

1-acetyl-isoquinoline oxime

Rendimiento 58.0%

Disolventes

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato reflux for 8 hours
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   OtroThe combined extracts were dried
4. 4
   Concentraciónconcentrated
5. 5
   Otrochromatographed

Procedimiento

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.

Fuente