Selenium Dioxide → 6-(3-Acetoxy-propoxy)-7-methoxy-1-(3-methoxy-benzoyl)-isoquinoline-4-carbaldehyde

HRID 1833171Notes

Reaction equation

HRID 1833171 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[C:15]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1)=[N:14][CH:13]=[C:12]2[CH:30]=[O:31])(=[O:3])[CH3:2].[Se](=O)=[O:33].C(OCC)(=O)C.CCCCCC>C(O)(=O)C>[C:1]([O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[C:15]([C:21](=[O:33])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1)=[N:14][CH:13]=[C:12]2[CH:30]=[O:31])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24007Selenium DioxideHCID 21226206Ethyl acetate hexaneHCID 220482406-(3-Acetoxy-propoxy)-7-methoxy-1-(3-methoxy-benzyl)-isoquinoline-4-carbaldehyde

Product 1

HCID 220483966-(3-Acetoxy-propoxy)-7-methoxy-1-(3-methoxy-benzoyl)-isoquinoline-4-carbaldehydeYield 97.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 6-(3-acetoxy-propoxy)-7-methoxy-1-(3-methoxy-benzyl)-isoquinoline-4-carbaldehyde (20 mg, 0.047 mmol) in acetic acid (1 mL) was added selenium dioxide (16 mg, 1.44 mmol). The reaction mixture was heated at 120° C. for 1 h. The solvent was evaporated and the residue was diluted with dichloromethane (30 mL). The organic layer was washed with saturated sodium bicarbonate solution (20 mL), saturated sodium chloride solution (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford a crude oil. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 40% ethyl acetate/hexane) afforded 6-(3-acetoxy-propoxy)-7-methoxy-1-(3-methoxy-benzoyl)-isoquinoline-4-carbaldehyde as a yellow solid (20 mg, 97% yield).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with dichloromethane (30 mL)
  3. washThe organic layer was washed with saturated sodium bicarbonate solution (20 mL), saturated sodium chloride solution (20 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a crude oil

Sources & evidence

ORD record
ord-f6e403c7f86545c6bba0331ae8aa2070
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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