1,4-Dioxane → HCID 86683822, compound

HRID 882084Notes

Reaction equation

HRID 882084 reaction equation
[Se].[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([C:16]#[N:17])[C:12]=1[N:13]([CH3:15])[CH3:14])[N:9]=[C:8]([CH3:18])[CH:7]=[CH:6]2.[O:19]1CCOCC1>>[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([C:16]#[N:17])[C:12]=1[N:13]([CH3:14])[CH3:15])[N:9]=[C:8]([CH:18]=[O:19])[CH:7]=[CH:6]2

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 6326970SeleniumHCID 67322122HCID 67322122, compound

Product 1

HCID 86683822HCID 86683822, compoundYield 72%

Procedure

Selenium dioxyde (50 mg, 0.45 mmol, 1.3 eq) in suspension in dioxane (1 mL) was heated at 60° C. The 6-bromo-7-dimethylamino-2-methylquinoline-8-carbonitrile (100 mg, 0.34 mmol, 1.0 eq) was then introduced and the mixture was left to react at 80° C. for 3 hours. After cooling to room temperature, the mixture was filtered on celite, eluted with dioxane and concentrated under reduced pressure. The crude product was precipitated from ether to afford 6-bromo-7-dimethylamino-2-formylquinolin-8-carbonitrile as an orange powder (74 mg, 72%).

Workup

  1. waitthe mixture was left
  2. customto react at 80° C. for 3 hours
  3. filtrationthe mixture was filtered on celite
  4. washeluted with dioxane
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was precipitated from ether

Sources & evidence

ORD record
ord-0fffeaa29565433f9ff8a24ca696b291
Source dataset
uspto-grants-2015_03
Patent number
US08993767B2

Reaction notes

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