Selenium Dioxide → HCID 22999310, compound

HRID 1166798Notes

Reaction equation

HRID 1166798 reaction equation
[Se](=O)=[O:2].[Cl:4][C:5]1[CH:23]=[CH:22][C:8]([CH2:9][O:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:20]=2[N:19]=[CH:18][CH:17]=[C:16]3[CH3:21])=[CH:7][CH:6]=1>O1CCOCC1.O>[Cl:4][C:5]1[CH:23]=[CH:22][C:8]([CH2:9][O:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:20]=2[N:19]=[CH:18][CH:17]=[C:16]3[CH:21]=[O:2])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 22999204HCID 22999204, compound

Product 1

HCID 22999310HCID 22999310, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
100 °C

Procedure

Selenium dioxide (620 mg, 5.6 mmol) was suspended in dioxane (5 mL); a few drops of water was added until a clear solution was obtained. The mixture was heated to 100° C. and 8-(4-chlorobenzyloxy)-4-methyl quinoline (1.6 g, 5.6 mmol) in dioxane (20 mL) was added dropwise during a period of 2 hours. The mixture kept at 100° C. for 4 hours, filtered hot and concentrated. The residue was treated with 1N HCl (200 ml), and filtered. The filtrate was neutralized with 3N NaOH, and extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried (Na2SO4), and concentrated. Recrystallization from toluene provided 1.02 g (62%) yellow needles.

Workup

  1. customwas obtained
  2. filtrationfiltered hot
  3. concentrationconcentrated
  4. additionThe residue was treated with 1N HCl (200 ml)
  5. filtrationfiltered
  6. extractionextracted with ethyl acetate (3×100 mL)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. concentrationconcentrated
  9. customRecrystallization from toluene

Sources & evidence

ORD record
ord-816731d49cec4e6a8c0eed74ae67dcd8
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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