Selenium Dioxide → HCID 178519499, compound

HRID 2165542Notes

Reaction equation

HRID 2165542 reaction equation
[CH2:1]([C:8]1[NH:9][C:10]2[C:19]3[CH:18]=[C:17]([F:20])[CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Se](=O)=[O:23]>O1CCOCC1>[C:1]([C:8]1[NH:9][C:10]2[C:19]3[CH:18]=[C:17]([F:20])[CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:21]=1)(=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 178505453HCID 178505453, compound

Product 1

HCID 178519499HCID 178519499, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 830 mg of 2-benzyl-8-fluoro-1H-imidazo[4,5-c]-quinoline (VII-1) in 50 ml of dioxane heated to 80° C. was added 1.07 g of selenium dioxide. The reaction mixture was refluxed for 1.5 hours. The resulting precipitate was immediately removed by filtration and concentrated under reduced pressure, and the residue obtained was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate. The organic layer was washed with water and saturated brine, and dried. The ethyl acetate was removed and the residue was chromatographed on a column of silica gel for purification. After elution with chloroform-methanol (30:1 v/v), 820 mg (yield 94%) of the compound (I d-1) was obtained as crystals. This was recrystallized from ethanol-chloroform to give light yellow crystals melting at 255°~256° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 1.5 hours
  2. customThe resulting precipitate was immediately removed by filtration
  3. concentrationconcentrated under reduced pressure
  4. customthe residue obtained
  5. customwas partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate
  6. washThe organic layer was washed with water and saturated brine
  7. customdried
  8. customThe ethyl acetate was removed
  9. customthe residue was chromatographed on a column of silica gel for purification
  10. washAfter elution with chloroform-methanol (30:1 v/v)

Sources & evidence

ORD record
ord-4c4ddb5f7a5a4519ad1136eabbd029a8
Source dataset
uspto-grants-1990_07
Patent number
US04940714

Reaction notes

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