Methyl morpholine oxide → 3-Methyl-4-nitrobenzaldehyde

HRID 1357753Notes

Reaction equation

HRID 1357753 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5][OH:6].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=[O:6]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 5913603-Methyl-4-nitrobenzyl alcohol

Product 1

HCID 111945283-Methyl-4-nitrobenzaldehydeYield 74%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyl-4-nitrobenzyl alcohol (3.0 g, 18 mmol), N-methylmorpholine-N-oxide (3.2 g, 27 mmol), and powdered 4A molecular sieves (8.98 g) in methylene chloride (40 mL) was added in one portion tetrapropylammonium perruthenate (0.315 g, 0.898 mmol), and the reaction stirred at room temperature. The reaction was filtered through silica gel, eluting with methylene chloride, solvent evaporated and the residue purified by flash chromatography to provide 2.2 g of the title compound. Examp~le 219B 5 9-(3-methyl-4-nitrophenyl)-2,3,5.6,7,9-hexahydrothieno[3.2-b]quinolin-8(4H)-one 1,1-dioxide 3-Methyl-4-nitrobenzaldehyde (0.99 g, 6.0 mmol) was processed according to the method of Example 11 5C to provide the title compound.

Workup

  1. filtrationThe reaction was filtered through silica gel
  2. washeluting with methylene chloride, solvent
  3. customevaporated
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-a7c4f60d6f274b29819e481570559597
Source dataset
uspto-grants-2003_07
Patent number
US06593335B1

Reaction notes

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