Selenium Dioxide → HCID 21034923, compound

HRID 1833118Notes

Reaction equation

HRID 1833118 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[C:9]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH:28]([CH3:30])[CH3:29])[CH:22]=2)=[N:8][CH:7]=1)=[O:5])[CH3:2].[Se](=O)=[O:32]>C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[C:9]([C:20](=[O:32])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH:28]([CH3:29])[CH3:30])[CH:22]=2)=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 21034913HCID 21034913, compound

Product 1

HCID 21034923HCID 21034923, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The above 1-(3-isopropoxybenzyl)-6,7-dimethoxyisoquinoline-4-carboxylic acid ethyl ester (2.20 g, 5.38 mmol) was dissolved into 100 ml of ethyl acetate. Then selenium dioxide (1.08 g, 9.73 mmol) was added and the mixture was refluxed for 30 minutes. The reaction mixture was filtered through a thin layer of silica gel. The filtrate was concentrated and then purified through a flash column chromatography using hexane and ethyl acetate (2.5/1 ratio) to give 1-(3-isopropoxybenzoyl)-6,7-dimethoxyisoquinoline-4-carboxylic acid ethyl ester as a solid (1.50 g, 66%).

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. filtrationThe reaction mixture was filtered through a thin layer of silica gel
  3. concentrationThe filtrate was concentrated
  4. custompurified through a flash column chromatography

Sources & evidence

ORD record
ord-242dfdb27f7e48b482560d8b524a6237
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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