Methyl morpholine oxide → HCID 84665874, compound

HRID 1026248Notes

Reaction equation

HRID 1026248 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH3:11])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].C[N+]1([O-])CC[O:19]CC1>C(#N)C>[CH2:10]([O:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]=[O:19])=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=1)[CH3:11]

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 68760715HCID 68760715, compound

Product 1

HCID 84665874HCID 84665874, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(bromomethyl)-4-ethoxy-2-nitrobenzene (11.3 g), 4-methylmorpholine N-oxide (10.1 g), molecular sieves 4A (11 g) and acetonitrile (220 ml) was stirred under an argon atmosphere at room temperature for 1 hr. The reaction mixture was filtered through celite, and the solvent of the filtrate was evaporated under reduced pressure. The residue was diluted with ethyl acetate, and the mixture was washed twice with water. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a yellow solid (5.65 g).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent of the filtrate was evaporated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washthe mixture was washed twice with water
  5. extractionThe separated aqueous layer was extracted again with ethyl acetate
  6. washThe combined organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c36c9e5867964260b9f7ebb2652c1d77
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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