Sodium periodate → 2-METHYLISONICOTINALDEHYDE

HRID 499614Notes

Reaction equation

HRID 499614 reaction equation
CN(C)C=[CH:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[CH:6]=1.I([O-])(=O)(=O)=[O:14].[Na+]>CO>[CH3:11][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][N:8]=1)[CH:4]=[O:14]

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 71437809N,N-dimethyl-2-(2-methyl-4-pyridyl)ethenamine

Product 1

HCID 27630002-METHYLISONICOTINALDEHYDEYield 78.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of N,N-dimethyl-2-(2-methyl-4-pyridyl)ethenamine (6.4 g, 39 mmol) in methanol (25 ml) was added dropwise to a mixture of sodium periodate (25.2 g, 117 mmol) and methanol (25 ml) at room temperature. The mixture was stirred at the same temperature for 1 hr. The precipitates were filtered off, and the filtrate was concentrated. The residue was combined with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated to give the titled compound (3.7 g, 78%).

Workup

  1. filtrationThe precipitates were filtered off
  2. concentrationthe filtrate was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-795073691615467b8278c0ecfabf54c3
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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