Selenium Dioxide → HCID 69551004, compound

HRID 1833252Notes

Reaction equation

HRID 1833252 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[C:8]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH:27]([CH2:29][CH3:30])[CH3:28])[CH:21]=2)=[N:7][CH:6]=1.[Se](=O)=[O:33].C(OCC)(=O)C.CCCCCC>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:31])[CH2:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[C:8]([C:19](=[O:33])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH:27]([CH2:29][CH3:30])[CH3:28])[CH:21]=2)=[N:7][CH:6]=1

Participants

5

Reactant 3

HCID 24007Selenium DioxideHCID 21034945HCID 21034945, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 69551004HCID 69551004, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of [1-(3-sec-butoxy-benzyl)-6,7-dimethoxy-isoquinolin-4-yl]-acetic acid methyl ester (200 mg, 0.47 mmol) in ethyl acetate (4 mL) was added selenium dioxide (65 mg, 0.59 mmol). The reaction mixture was heated at 85° C. for 1 hr. The solvent was evaporated and afford a crude product. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 40% ethyl acetate/hexane) afforded [1-(3-sec-butoxy-benzoyl)-6,7-dimethoxy-isoquinolin-4-yl]-acetic acid methyl ester as a light brown oil (170 mg, 83% yield).

Workup

  1. customThe solvent was evaporated
  2. customafford a crude product

Sources & evidence

ORD record
ord-8053724d2ed344dcba91bac038a58ca0
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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