Methyl morpholine oxide → 1006598-63-5

HRID 2071163Notes

Reaction equation

HRID 2071163 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][OH:13])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:12]=[O:13])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 73995155HCID 73995155, compound

Product 1

HCID 722138911006598-63-5Yield 43%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirring mixture of 3.6 g (17.9 mmol) of methyl 2-chloro-6-(hydroxymethyl)isonicotinate, 8.9 g of 4A powdered molecular sieves, 3.1 g (26.5 mmol) of NMO in 55 mL of CH2Cl2 was added (after about 10 min.) 659 mg (1.87 mmol) of TPAP. The mixture began to gently reflux, and the mixture was stirred for 75 min., filtered through Celite, and concentrated. Purification by flash silica gel chromatography (10% EtOAc/hexanes) provided 1.53 g of methyl 2-chloro-6-formylisonicotinate in 43% yield as an off-white solid.

Workup

  1. temperatureto gently reflux
  2. filtrationfiltered through Celite
  3. concentrationconcentrated
  4. customPurification by flash silica gel chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ecc2e51034f84bdf86ef0732edbde296
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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