Selenium Dioxide → HCID 22048267, compound

HRID 1833115Notes

Reaction equation

HRID 1833115 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][CH:26]=1)[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10]([CH2:21][C:22]#[N:23])=[CH:9][N:8]=1.[Se](=O)=[O:28]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][CH:26]=1)[C:6]([C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10]([CH2:21][C:22]#[N:23])=[CH:9][N:8]=1)=[O:28]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 22048334HCID 22048334, compound

Product 1

HCID 22048267HCID 22048267, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The above 1-(3-methoxybenzyl)-4-cyanomethyl-6,7-dimethoxyisoquinoline (152.7 mg, 0.438 mmol) was dissolved in 10 ml of ethyl acetate, then selenium dioxide (48.8 mg, 58.8 mg, 0.529 mmol) was added. The mixture was refluxed for 1 hr. The crude mixture was filtered through a thin layer of silica gel and washed with ethyl acetate. After the evaporation of solvents, the residue was purified through a flash column chromatography using ethyl acetate and hexane (2/1) to give 1-(3-methoxybenzoyl)-4-cyanomethyl-6,7-dimethoxyisoquinoline as a solid (68 mg, 42.8%).

Workup

  1. temperatureThe mixture was refluxed for 1 hr
  2. filtrationThe crude mixture was filtered through a thin layer of silica gel
  3. washwashed with ethyl acetate
  4. customAfter the evaporation of solvents
  5. customthe residue was purified through a flash column chromatography

Sources & evidence

ORD record
ord-1b1c6f5a422d408b81c2e9cddff3ce8e
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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