6-Chloro-4-(2-propen-1-yl)-1,2,4-benzotriazin-3(4H)-one 1-oxide → (6-Chloro-1-oxido-3-oxo-1,2,4-benzotriazin-4(3H)-yl)acetaldehyde

HRID 657020Notes

Reaction equation

HRID 657020 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N+:10]([O-:11])=[N:9][C:8](=[O:12])[N:7]([CH2:13][CH:14]=C)[C:6]=2[CH:16]=1.I([O-])(=O)(=O)=[O:18].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N+:10]([O-:11])=[N:9][C:8](=[O:12])[N:7]([CH2:13][CH:14]=[O:18])[C:6]=2[CH:16]=1

Participants

6

Reactant 2

HCID 144230516-Chloro-4-(2-propen-1-yl)-1,2,4-benzotriazin-3(4H)-one 1-oxideHCID 23667635Sodium periodate

Product 1

HCID 86635335(6-Chloro-1-oxido-3-oxo-1,2,4-benzotriazin-4(3H)-yl)acetaldehydeYield 85%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

6-Chloro-4-(2-propen-1-yl)-1,2,4-benzotriazin-3(4H)-one 1-oxide (104 mg, 0.438 mmol) was dissolved in 1,4-dioxane (4 ml) and water (2 ml). Sodium periodate (234 mg, 1.096 mmol) was added, followed by osmium tetroxide (0.09 ml of 4% aqueous solution). The mixture stirred at rt for 6 h, and then extracted with 20% MeOH/DCM (3×100 ml). The organic extracts were combined, dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure to give (6-Chloro-1-oxido-3-oxo-1,2,4-benzotriazin-4(3H)-yl)acetaldehyde as an impure yellow oil (89 mg, 85%).

Workup

  1. extractionextracted with 20% MeOH/DCM (3×100 ml)
  2. dry with materialdried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d628fc3abc6d4dc7b43b55a3fc0ebd66
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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