Selenium Dioxide → HCID 12045063, compound

HRID 1829709Notes

Reaction equation

HRID 1829709 reaction equation
[CH3:1][C:2]([CH3:25])([CH3:24])[C:3]([O:5][C:6]1[C:7]([C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2)=[O:4].[Se](=O)=[O:27]>O1CCOCC1>[CH3:1][C:2]([CH3:24])([CH3:25])[C:3]([O:5][C:6]1[C:7]([C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH:16]=[O:27])[CH:12]=[CH:11]2)=[O:4]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 12045062HCID 12045062, compound

Product 1

HCID 12045063HCID 12045063, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of the preceding diester 3 (step 2) (11.5 g, 34 mmol) and selenium dioxide (6.7 g, 60 mmol) in 50 ml of 1,4-dioxane is heated under reflux for 12 hours. After cooling to 20° C., the reaction mixture is filtered on Celite® and concentrated under reduced pressure. The residue is chromatographed on a silica column, eluting a 4/1 cyclohexane/ethyl acetate mixture so as to give 8.6 g (71%) of n-butyl 8-(2,2-dimethylpropionyloxy)-2-formylquinoline-7-carboxylate 4. White solid.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 12 hours
  3. filtrationthe reaction mixture is filtered on Celite®
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed on a silica column
  6. washeluting a 4/1 cyclohexane/ethyl acetate mixture so as

Sources & evidence

ORD record
ord-35e1edbe4e3049e18973e52db046d8d5
Source dataset
uspto-grants-2006_06
Patent number
US07064133B2

Reaction notes

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