Hydrogen Peroxide → 4-carboxy-isoquinoline N-oxide

HRID 1200034Notes

Reaction equation

HRID 1200034 reaction equation
[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[N:6][CH:5]=1)([OH:3])=[O:2].[OH:14]O>C(O)(=O)C>[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[N+:6]([O-:14])[CH:5]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 459768Isoquinoline-4-carboxylic acid

Product 1

HCID 537062234-carboxy-isoquinoline N-oxide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Carboxy-isoquinoline [J. Amer. Chem. Soc. 67, 1268 (1945)](10 g, 0.058 mol) is refluxed in 100 ml of acetic acid containing 13 ml of hydrogen peroxide (30%) overnight. After cooling, the solution is evaporated to dryness and the residue is purified by column chromatography (ethyl acetate/methanol/formic acid 3:2:1) to yield 4-carboxy-isoquinoline N-oxide, m.p. 280°-283°, Rf =0.3.

Workup

  1. temperatureAfter cooling
  2. customthe solution is evaporated to dryness
  3. customthe residue is purified by column chromatography (ethyl acetate/methanol/formic acid 3:2:1)

Sources & evidence

ORD record
ord-55f40506312d4329b1bf8e23cf4be1d9
Source dataset
uspto-grants-1990_02
Patent number
US04904675

Reaction notes

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