Selenium Dioxide → HCID 57815212, compound

HRID 1510698Notes

Reaction equation

HRID 1510698 reaction equation
[CH3:1][C:2]1[N:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[Se](=O)=[O:14]>O1CCOCC1>[O:12]=[C:8]1[NH:9][C:10]2[N:11]=[C:2]([CH:1]=[O:14])[CH:3]=[CH:4][C:5]=2[CH:6]=[CH:7]1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 578152267-Methyl-3,4-dihydro-1,8-naphthyridin-2(1H)-one

Product 1

HCID 57815212HCID 57815212, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.90 g of 7-methyl-3,4-dihydro-1,8-naphthyridin-2(1H)-one in 150 mL of dioxane was heated under reflux while dividedly adding 25.7 g of selenium dioxide, and the mixture was stirred for 10 days. The insoluble substance was filtered off with celite, and the solvent was distilled off under reduced pressure. To the resultant residue, 2-propanol was added, and the solid was filtered off. The solid thus obtained was purified by silica gel column chromatography using an eluent of chloroform:methanol=20:1, and ethyl acetate was added thereto, and the solid was filtered off to obtain 0.48 g of 7-oxo-7,8-dihydro-1,8-naphthyridine-2-carbaldehyde as a light orange solid.

Workup

  1. temperatureunder reflux
  2. filtrationThe insoluble substance was filtered off with celite
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionTo the resultant residue, 2-propanol was added
  5. filtrationthe solid was filtered off
  6. customThe solid thus obtained
  7. customwas purified by silica gel column chromatography
  8. additionmethanol=20:1, and ethyl acetate was added
  9. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-9a77ca102ef9471084f9c6d6f1756914
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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