Selenium Dioxide → HCID 69550663, compound

HRID 1833276Notes

Reaction equation

HRID 1833276 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]=[CH:23][CH:22]=2)=[N:8][CH:7]=1)=[O:5])[CH3:2].[Se](=O)=[O:28]>C(O)(=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:28])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 69551722HCID 69551722, compound

Product 1

HCID 69550663HCID 69550663, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The above 1-benzyl-6,7-dimethoxyisoquinoline-4-carboxylic acid ethyl ester (77.1 mg, 0.22 mmol) was dissolved in 5 ml of acetic acid. Then selenium dioxide (36.6 mg, 1.50 eq) was added and the mixture was refluxed for 1 hr until no more starting material was left. The mixture was evaporated to dryness and the residue was extracted with ethyl acetate and sodium bicarbonate solution. The organic layer was dried over sodium sulfate and then concentrated. The residue was dissolved in 5 ml of ethyl acetate and the solution was passed through a layer of silica gel. The solution was concentrated go give a pure 1-benzoyl-6,7-dimethoxyisoquinoline-4-carboxylic acid ethyl ester (70 mg, 87%).

Workup

  1. temperaturethe mixture was refluxed for 1 hr until
  2. waitwas left
  3. customThe mixture was evaporated to dryness
  4. extractionthe residue was extracted with ethyl acetate and sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in 5 ml of ethyl acetate
  8. concentrationThe solution was concentrated go

Sources & evidence

ORD record
ord-3168b03b7ebe45f1b45790c5e180d747
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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