1-Methylisoquinoline → Isoquinoline-1-carbaldehyde

HRID 1372765Notes

Reaction equation

HRID 1372765 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[Se](=O)=[O:13]>O1CCOCC1>[C:2]1([CH:1]=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 155921-MethylisoquinolineHCID 24007Selenium Dioxide

Product 1

HCID 265306Isoquinoline-1-carbaldehydeYield 77%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In 1,4-dioxane (20 ml) was dissolved 1-methylisoquinoline (300 mg, 2.10 mmol). To the resulting solution was added selenium dioxide (323 mg, 2.91 mmol), followed by heating under reflux for 1.5 hours under a nitrogen gas stream. After cooling to room temperature, the reaction mixture was filtered through Celite. The filtrate was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (5:1, v/v) eluate fractions, 1-isoquinolinecarbaldehyde (252 mg, 77%) was obtained as a white solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1.5 hours under a nitrogen gas stream
  3. filtrationthe reaction mixture was filtered through Celite
  4. distillationThe filtrate was distilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (5:1

Sources & evidence

ORD record
ord-5acbe87a705c45d6ad3fd9f5631b4a5d
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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