Dimethyl Sulfoxide → 4-(3-Methyl-4-nitrophenyl)morpholine

HRID 912329Notes

Reaction equation

HRID 912329 reaction equation
CS(C)=O.F[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([CH3:15])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>O>[CH3:15][C:8]1[CH:7]=[C:6]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:11]=[CH:10][C:9]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 112645284-(3-Methyl-4-nitrophenyl)morpholineYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a DMSO solution (8 ml) of 4-fluoro-2-methyl-1-nitro-benzene (500 mg), potassium carbonate (668 mg) and morpholine (0.42 ml) were added, followed by stirring at 80° C. for 18 hours. This was cooled to room temperature, and water (30 ml) was added, followed by extraction with ethyl acetate (50 ml×2). The organic layer was washed with saturated aqueous sodium chloride solution, followed by drying over magnesium sulfate. After the magnesium sulfate was filtered off, the solvent was distilled off under reduced pressure, to obtain the desired compound as a yellow solid (680 mg, 95%).

Workup

  1. temperatureThis was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate (50 ml×2)
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialby drying over magnesium sulfate
  5. filtrationAfter the magnesium sulfate was filtered off
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c96970a1d30d412fbad3d297832e48a9
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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