Methyl morpholine oxide → 5,6-Dichloropyridine-3-carbaldehyde

HRID 420708Notes

Reaction equation

HRID 420708 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[N:6][C:7]=1[Cl:8].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[O:10])[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 21882961(5,6-Dichloropyridin-3-yl)methanol

Product 1

HCID 115356545,6-Dichloropyridine-3-carbaldehydeYield 22.3%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (5,6-dichloro-3-pyridinyl)methanol (200 mg) in DCM, molecular sieves (3 Å) (55 mg) and 4-methyl-morpholine-N-oxide (198 mg) was added and stirred at room temperature for 10 minutes. Then tetra-n-propylammonium perruthenate (VII) (38 mg) was added and stirred overnight. The reaction mixture was filtered and the solvent was evaporated to dryness under vacuum. The residue obtained was purified by chromatography column on silica gel using a mixture of EtOAc/hexane as eluent to give 44 mg (22%) of the title compound.

Workup

  1. stirringstirred overnight
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was evaporated to dryness under vacuum
  4. customThe residue obtained
  5. customwas purified by chromatography column on silica gel using
  6. additiona mixture of EtOAc/hexane as eluent

Sources & evidence

ORD record
ord-720c4979382247dbb3af202bdd19cdbd
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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