Reaction #1026

Reaction equation

1-acetyl-isoquinoline

hydroxylamine

sodium acetate

methanol

→

1-acetyl-isoquinoline oxime

Yield 58.0%

Solvents

water

water

Conditions

Workup

1. 1
   Temperatureto reflux for 8 hours
2. 2
   Extractionextracted with ethyl acetate
3. 3
   OtherThe combined extracts were dried
4. 4
   Concentrationconcentrated
5. 5
   Otherchromatographed

Procedure

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