Reaction #1028

Reaction equation

3-acetyl-isoquinoline

hydroxylamine

sodium acetate

→

3-acetyl-isoquinoline oxime

Yield 89.0%

Solvents

water

methanol

water

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureto reflux for 1.5 hours
3. 3
   Extractionextracted with ethyl acetate
4. 4
   OtherThe combined extracts were dried
5. 5
   Concentrationconcentrated
6. 6
   Othertriturated with hexane

Procedure

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.

Source