Isoquinoline → isoquinolin-N-oxide

HRID 44819

Reaction equation

HRID 44819 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C1C=C(Cl)C=C(C(OO)=[O:19])C=1>C(Cl)(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N+:2]=1[O-:19]

Participants

4

Reactant 2

HCID 8405IsoquinolineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 290378isoquinolin-N-oxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of isoquinoline (1-Im-9, 5 g, 1.0 eq) in 50 mL of CHCl3, mCPBA (2.0 eq) was added. The mixture was stirred at rt for 1 h. The reaction was washed with 5% aqueous Na2SO3 and aqueous Na2CO3, then concentrated and the residue was purified by silica column chromatography to give isoquinoline 2-oxide (2-Im-9).

Workup

  1. washThe reaction was washed with 5% aqueous Na2SO3 and aqueous Na2CO3
  2. concentrationconcentrated
  3. customthe residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-e6b18eeb6a8c4466b0200d7320f148d3
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Linked notes

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