Water → (8-Ethyl-7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde

HRID 656906Notes

Reaction equation

HRID 656906 reaction equation
[CH2:1]([C:3]1[C:4]([F:17])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]([CH2:13][CH:14]=C)[C:10](=[O:16])[CH:9]=[CH:8]2)[CH3:2].O.I([O-])(=O)(=O)=[O:20].[Na+]>O1CCOCC1.[Cl-].[Na+].O.CCOC(C)=O.[Os](=O)(=O)(=O)=O>[CH2:1]([C:3]1[C:4]([F:17])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]([CH2:13][CH:14]=[O:20])[C:10](=[O:16])[CH:9]=[CH:8]2)[CH3:2]

Participants

8

Reactant 3

HCID 962Water2×HCID 23667635Sodium periodateHCID 689929808-Ethyl-7-fluoro-1-(2-propen-1-yl)-1,5-naphthyridin-2(1H)-one

Product 1

HCID 86635314(8-Ethyl-7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehydeYield 91.8%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

8-ethyl-7-fluoro-1-(2-propen-1-yl)-1,5-naphthyridin-2(1H)-one (0.181 g, 0.781 mmol) was dissolved in 1,4-dioxane (4.0 mL) and water (3.5 ml) at rt under argon. Then sodium periodate (0.418 g, 1.95 mmol) was added followed by osmium tetroxide (0.175 mL of 4% aqueous solution). After 10 mins a white precipitate came out of solution, further addition of water (2 ml) was required to re-dissolve everything. After the reaction had been left stirring at rt overnight, it was then diluted with brine (20 ml) and EtOAc (20 ml). The aqueous was then separated and washed a further with EtOAc (3×20 ml). The organic layers were then combined, dried using sodium sulphate, filtered and solvent removed to give the crude product as a yellow solid (0.168 g).

Workup

  1. customat rt
  2. dissolutionto re-dissolve everything
  3. waitAfter the reaction had been left
  4. customThe aqueous was then separated
  5. washwashed a further with EtOAc (3×20 ml)
  6. customdried
  7. filtrationfiltered
  8. customsolvent removed

Sources & evidence

ORD record
ord-44d9be1ed69a4641af7f582606d42665
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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