Selenium Dioxide → HCID 22048437, compound

HRID 1833265Notes

Reaction equation

HRID 1833265 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:25]=[CH:26][CH:27]=1)[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[C:12]([CH:23]=[O:24])=[CH:11][N:10]=1)([CH3:3])[CH3:2].[Se](=O)=[O:29]>C(OCC)(=O)C>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:25]=[CH:26][CH:27]=1)[C:8]([C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[C:12]([CH:23]=[O:24])=[CH:11][N:10]=1)=[O:29])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 22048313HCID 22048313, compound

Product 1

HCID 22048437HCID 22048437, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(3-isopropoxy-benzyl)-6,7-dimethoxy-isoquinoline-4-carbaldehyde (200 mg, 0.547 mmol) and selenium dioxide (121 mg, 1.09 mmol) in ethyl acetate was refluxed for 45 min. The mixture was cooled and filtered through celite. The celite was washed well with ethyl acetate and the combined filtrates were concentrated in vacuo to afford 1-(3-isopropoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carbaldehyde (160 mg, 77%) as a light yellow solid that was used without further purification: APCI-MS (M+H+) m/e 380; 1H NMR (300 MHz) compatible.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through celite
  3. washThe celite was washed well with ethyl acetate
  4. concentrationthe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-a4469e207d184f5084a72186579cf2ea
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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