Selenium Dioxide → HCID 12875021, compound

HRID 847774Notes

Reaction equation

HRID 847774 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].S1(CCCC1)(=O)=[O:24].[Se](=O)=O>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

5

Reactant 3

HCID 24007Selenium DioxideHCID 31347SulfolaneHCID 12875020HCID 12875020, compound2×

Product 1

HCID 12875021HCID 12875021, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 30.4 g of ethyl 1,4-dihydro-6-ethoxy-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate (Compound VIII where R1 =R2 =R3 =C2H5) and 100 ml of sulfolane was stirred at 140°-145° C. and 22 g of selenium dioxide in limited amounts was added thereto. After reacting the mixture under the same conditions for 5 hours and then allowing it to cool, chloroform was added thereto. The insoluble materials were removed by filtration. The filtrate was washed successively with 3% sodium carbonate solution, water, dried over anhydrous sodium sulfate and evaporated. To the residue was added isopropanol and the precipitated crystals were collected by filtration to obtain 22.0 g of ethyl 1,4-dihydro-6-ethoxy-1-ethyl-7-formyl-4-oxo-1,8-naphthyridine-3-carboxylate, m.p. 169°-170° C.

Workup

  1. customfor 5 hours
  2. temperatureto cool
  3. customThe insoluble materials were removed by filtration
  4. washThe filtrate was washed successively with 3% sodium carbonate solution, water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. additionTo the residue was added isopropanol
  8. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-23581204fec040bf92d1167731aa757c
Source dataset
uspto-grants-1981_10
Patent number
US04293695

Reaction notes

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