Hydroxylamine → 3-Acetyl-isoquinoline oxime

HRID 932

Reaction equation

HRID 932 reaction equation
[C:1]([C:4]1[N:5]=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)(=O)[CH3:2].[NH2:14][OH:15].C([O-])(=O)C.[Na+]>CO.O>[C:1](=[N:14][OH:15])([C:4]1[N:5]=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:2]

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 517045Sodium AcetateHCID 112752751-(Isoquinolin-3-yl)ethan-1-one

Product 1

HCID 1363959913-Acetyl-isoquinoline oximeYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

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.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 hours
  3. extractionextracted with ethyl acetate
  4. customThe combined extracts were dried
  5. concentrationconcentrated
  6. customtriturated with hexane

Sources & evidence

ORD record
ord-6886621a94c642309e84fee2699ce813
Source dataset
uspto-grants-1998_03
Patent number
US05723473

Linked notes

Loading…