Selenium Dioxide → HCID 12875021, compound

HRID 847772Notes

Reaction equation

HRID 847772 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[N:12][C:13]=1[CH3:14])[N:10]([CH2:15][CH3:16])[CH:9]=[C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:7]2=[O:22])[CH3:2].[Se](=O)=[O:24]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[N:12][C:13]=1[CH:14]=[O:24])[N:10]([CH2:15][CH3:16])[CH:9]=[C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:7]2=[O:22])[CH3:2]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 12875020HCID 12875020, compound

Product 1

HCID 12875021HCID 12875021, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

20.2 g of the Compound VIII obtained as above was heated at 175°-185° C. under a nitrogen stream to melt and 10 g of selenium dioxide was added in several portions. Under a nitrogen stream, the mixture was reacted under the same conditions for 20 minutes. After allowing to cool, chloroform was added to the reaction mixture and the insoluble materials were removed by filtration and the filtrate was concentrated in vacuo. The resulting residue was recrystallized from ethanol to yield 13.2 g of ethyl 1,4-dihydro-6-ethoxy-1-ethyl-7-formyl-4-oxo-1,8-naphthyridine-3-carboxylate having a melting point of 169°-170° C.

Workup

  1. temperatureabove was heated at 175°-185° C. under a nitrogen stream
  2. customUnder a nitrogen stream, the mixture was reacted under the same conditions for 20 minutes
  3. temperatureto cool
  4. customthe insoluble materials were removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-3ee6a090bdc942d084a73b1ead30fea6
Source dataset
uspto-grants-1981_10
Patent number
US04293695

Reaction notes

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