Methyl morpholine oxide → N-(5-Formylpyridin-2-yl)acetamide

HRID 242155Notes

Reaction equation

HRID 242155 reaction equation
C[N+]1([O-])CCOCC1.[OH:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([NH:17][C:18](=[O:20])[CH3:19])=[N:15][CH:16]=1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH:10]([C:11]1[CH:12]=[CH:13][C:14]([NH:17][C:18](=[O:20])[CH3:19])=[N:15][CH:16]=1)=[O:9]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 54303828N-[5-(Hydroxymethyl)-2-pyridinyl]acetamide

Product 1

HCID 22113222N-(5-Formylpyridin-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

500 mg of powdered molecular sieve (4 Å) and 113 mg (0.96 mmol) of N-methylmorpholine N-oxide are added to a solution of the crude product from example 18A in 2 ml of dry dichloromethane. 11 mg (0.03 mmol) of tetrapropylammonium perruthenate are then added to the reaction mixture, which is then stirred at RT for 1 h. The mixture is purified directly by chromatography on a silica gel fritte (mobile phase: gradient dichloromethane/ethanol 100:1→10:1). All product-containing fractions are combined, the solvent is removed on a rotary evaporator and the residue is purified further by another silica gel chromatography (mobile phase: gradient dichloromethane/ethanol 200:1→5:1).

Workup

  1. customThe mixture is purified directly by chromatography on a silica gel fritte (mobile phase: gradient dichloromethane/ethanol 100:1→10:1)
  2. customthe solvent is removed on a rotary evaporator
  3. customthe residue is purified further by another silica gel chromatography (mobile phase: gradient dichloromethane/ethanol 200:1→5:1)

Sources & evidence

ORD record
ord-bda9deef05e44e38a82bcd8a9e84e2dd
Source dataset
uspto-grants-2014_02
Patent number
US08653109B2

Reaction notes

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