Sodium periodate → HCID 86635319, compound

HRID 656928Notes

Reaction equation

HRID 656928 reaction equation
[O:1]=[C:2]1[N:11]([CH2:12][CH:13]=C)[C:10]2[N:9]=[C:8]([C:15]#[N:16])[CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3]1.I([O-])(=O)(=O)=[O:18].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[O:1]=[C:2]1[N:11]([CH2:12][CH:13]=[O:18])[C:10]2[N:9]=[C:8]([C:15]#[N:16])[CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3]1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 68809622HCID 68809622, compound

Product 1

HCID 86635319HCID 86635319, compoundYield 112%

Reagents, catalysts & solvents 3

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

Procedure

7-Oxo-8-(2-propen-1-yl)-7,8-dihydro-1,8-naphthyridine-2-carbonitrile (374 mg, 1.773 mmol) was dissolved in 1,4-dioxane (10 ml) and water (10 ml). Sodium periodate (948 mg, 4.433 mmol) was added, followed by osmium tetroxide (0.38 ml of 4% aqueous solution). The mixture stirred at rt for 1 h, water (40 ml) was added the mixture was stirred for a further 1 h. The reaction was concentrated to about 50 ml and 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 7-oxo-8-(2-oxoethyl)-7,8-dihydro-1,8-naphthyridine-2-carbonitrile as an impure brown solid (423 mg, 112%).

Workup

  1. stirringwas stirred for a further 1 h
  2. concentrationThe reaction was concentrated to about 50 ml
  3. extractionextracted with 20% MeOH/DCM (3×100 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-dc690a08cfed4d2dbee5a80fd13ccbbf
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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