Sodium periodate → 1-oxo-1,2,3,4-tetrahydroisoquinoline-7-carbaldehyde

HRID 2233210Notes

Reaction equation

HRID 2233210 reaction equation
[CH:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][C:10]2=[O:13])=[CH:5][CH:4]=1)=C.I([O-])(=O)(=O)=[O:15].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[O:13]=[C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([CH:1]=[O:15])[CH:12]=2)[CH2:7][CH2:8][NH:9]1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 574868957-Vinyl-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 642240451-oxo-1,2,3,4-tetrahydroisoquinoline-7-carbaldehydeYield 57%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 7-ethenyl-3,4-dihydro-1(2H)-isoquinolinone (232 mg, 1.341 mmol) in 1,4-dioxane (15 ml) and water (3 ml) at 0° C. was added sodium periodate (660 mg, 3.08 mmol) and osmium tetroxide (1.5 ml of a 4% aqueous solution). The reaction mixture was warmed to room temperature and stirred for 0.5 h before evaporation of the reaction mixture. The residue was dissolved in 1,4-dioxane (50 ml) and evaporated again. The mixture was then dissolved in dichloromethane (100 ml), dried with magnesium sulphate and evaporated. Chromatography on silica, eluting with 0-100% ethyl acetate/hexane, gave the product (133 mg, 57%).

Workup

  1. customevaporated again
  2. dissolutionThe mixture was then dissolved in dichloromethane (100 ml)
  3. dry with materialdried with magnesium sulphate
  4. customevaporated
  5. washChromatography on silica, eluting with 0-100% ethyl acetate/hexane

Sources & evidence

ORD record
ord-75019ced87c143bda42c419fc7758dc7
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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