Sodium periodate → (7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde

HRID 656879Notes

Reaction equation

HRID 656879 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=C)=[N:5][CH:4]=1.I([O-])(=O)(=O)=[O:18].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=[O:18])=[N:5][CH:4]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 585793327-Methoxy-1-(2-propen-1-yl)-1,5-naphthyridin-2(1H)-one

Product 1

HCID 57815194(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

7-(Methoxy)-1-(2-propen-1-yl)-1,5-naphthyridin-2(1H)-one (5.046 g, 23.361 mmol) was dissolved in 1,4-dioxane (100 mL) and water (100 mL). Sodium periodate (12.49 g, 58.402 mmol) was added, followed by osmium tetroxide (5 mL of 4% aqueous solution). The mixture stirred at rt for 1 h, water (200 ml) was added the mixture was stirred for a further 1 h. The reaction was concentrated to about 300 ml and extracted with 20% MeOH/DCM (3×400 ml). The organic extracts were combined, dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure to give [7-(methoxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]acetaldehyde (as the methyl hemiacetal) as a yellow solid (3.807 g, 75%).

Workup

  1. stirringwas stirred for a further 1 h
  2. concentrationThe reaction was concentrated to about 300 ml
  3. extractionextracted with 20% MeOH/DCM (3×400 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5b8bc75435244d93b20a5c0929b72fba
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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