Hydrogen Peroxide → Isoquinoline, 3,4-dihydro-, 2-oxide

HRID 1708476Notes

Reaction equation

HRID 1708476 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[Se](=O)=[O:12].OO>CO>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N+:2]=1[O-:12]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 70461,2,3,4-TetrahydroisoquinolineHCID 24007Selenium Dioxide

Product 1

HCID 141110Isoquinoline, 3,4-dihydro-, 2-oxideYield 1,261.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.00 g of 1,2,3,4-tetrahydroisoquinoline, 0.042 g of selenium dioxide, 2.30 ml of 30% hydrogen peroxide in 20 ml of methanol is stirred at room temperature for 20 hours. The reaction mixture is concentrated in vacuo to a residue which is diluted with water and extracted with chloroform. The organic layer is dried and evaporated in vacuo to a residue which is purified by column chromatography on silica gel by elution with 99:1 methanol-chloroform to give 0.703 g of the desired product as a solid.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo to a residue which
  2. additionis diluted with water
  3. extractionextracted with chloroform
  4. customThe organic layer is dried
  5. customevaporated in vacuo to a residue which
  6. customis purified by column chromatography on silica gel by elution with 99:1 methanol-chloroform

Sources & evidence

ORD record
ord-0ba1dc5ca3f649e7b86b2b2d9eb281f9
Source dataset
uspto-grants-1994_10
Patent number
US05358951

Reaction notes

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