Hydroxylamine → 1-Acetyl-isoquinoline oxime

HRID 930

Reaction equation

HRID 930 reaction equation
[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][N:5]=1)(=O)[CH3:2].[NH2:14][OH:15].C([O-])(=O)C.[Na+].CO>O>[C:1](=[N:14][OH:15])([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][N:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 887MethanolHCID 517045Sodium AcetateHCID 131572141-(Isoquinolin-1-yl)ethan-1-one

Product 1

HCID 6392871-Acetyl-isoquinoline oximeYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

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.

Workup

  1. temperatureto reflux for 8 hours
  2. extractionextracted with ethyl acetate
  3. customThe combined extracts were dried
  4. concentrationconcentrated
  5. customchromatographed

Sources & evidence

ORD record
ord-1c93b7108442465f805b25dd4eb5e4ed
Source dataset
uspto-grants-1998_03
Patent number
US05723473

Linked notes

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