Selenium Dioxide → HCID 14091438, compound

HRID 255500Notes

Reaction equation

HRID 255500 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([CH2:22][CH2:23][CH3:24])[C:8]3[O:15][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][C:12](=[O:21])[C:9]=3[CH:10]=2)[N:5]=[C:4]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:3]=1.[Se](=O)=[O:31]>C(O)(=O)C>[CH:1]([C:2]1[C:11]2[C:6](=[C:7]([CH2:22][CH2:23][CH3:24])[C:8]3[O:15][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][C:12](=[O:21])[C:9]=3[CH:10]=2)[N:5]=[C:4]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:3]=1)=[O:31]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 13543998HCID 13543998, compound

Product 1

HCID 14091438HCID 14091438, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of diethyl 6-methyl-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylate (19 g), selenium dioxide (20.99 g), and glacial acetic acid (950 ml) was heated on a steam bath with stirring for 2 hours. The resulting suspension was cooled, filtered and poured into brine (8 l). The resulting precipitate was filtered off and the crude product dissolved in CH2Cl2, filtered and evaporated to dryness to give 20.5 g of the crude product (20.5 g). This product was chromatographed using 25:1 CH2Cl2 : ethyl acetate as the solvent, yielding 13.95 g of required product (71%).

Workup

  1. temperaturewas heated on a steam bath
  2. temperatureThe resulting suspension was cooled
  3. filtrationfiltered
  4. additionpoured into brine (8 l)
  5. filtrationThe resulting precipitate was filtered off
  6. dissolutionthe crude product dissolved in CH2Cl2
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customto give 20.5 g of the crude product (20.5 g)
  10. customThis product was chromatographed

Sources & evidence

ORD record
ord-e964d1ba7251468e89276ae6cadf9be2
Source dataset
uspto-grants-1987_10
Patent number
US04698345

Reaction notes

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