Methyl morpholine oxide → 2-Fluoro-4-(methylamino)benzaldehyde

HRID 2252055Notes

Reaction equation

HRID 2252055 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][OH:11].C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]=[O:11]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 17981859[2-Fluoro-4-(methylamino)phenyl]methanol

Product 1

HCID 179817032-Fluoro-4-(methylamino)benzaldehydeYield 140.7%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Add tetrapropylammonium perruthenate (0.35 g) to a mixture of (2-fluoro-4-methylamino-phenyl)-methanol (0.18 g), 4-methylmorpholine N-oxide (0.38 g) and freshly activated powdered molecular sieves (0.30 g) in dry dichloromethane (10 mL) at room temperature under a nitrogen atmosphere. Stir for 30 minutes and add more dichloromethane and filter through a florisil-Celite® pad. Concentrate under reduced pressure to provide (0.25 g, 76%) of the title compound as an oil.

Workup

  1. customat room temperature
  2. filtrationfilter through a florisil-Celite® pad
  3. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-1749775d50074647905954e0ea5b282e
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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