Methyl iodide → N-(3-Methoxy-4-nitrophenyl)acetamide

HRID 1773556Notes

Reaction equation

HRID 1773556 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[C:15](=O)([O-])[O-].[K+].[K+].CI.C(OCC)(=O)C>[Cl-].[Na+].O>[CH3:15][O:1][C:2]1[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 6328Methyl iodide2×HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 10176525Acetamide, N-(3-hydroxy-4-nitrophenyl)-

Product 1

HCID 13734467N-(3-Methoxy-4-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of N-(3-hydroxy-4-nitro-phenyl)-acetamide (2 g, 10.15 mmol) in anhydrous N,N-dimethylormamide (5 mL) was added potassium carbonate (2.6 g, 18.88 mmol) followed by methyl iodide (0.71 mL, 11.16 mmol) and the reaction mixture was stirred at room temperature for 1 hour. A second aliquot of methyl iodide (0.15 mL) was then added and the resulting mixture was stirred for 1 hour. Ethyl acetate (100 mL) and brine (100 mL) were added, the organic layer was separated, washed twice with water, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give N-(3-methoxy-4-nitro-phenyl)-acetamide.

Workup

  1. stirringthe resulting mixture was stirred for 1 hour
  2. customthe organic layer was separated
  3. washwashed twice with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-25166f50f9cb4497949ed93b617d5575
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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