Acetic Anhydride → N-(2-Methoxy-6-methylphenyl)acetamide

HRID 1351991Notes

Reaction equation

HRID 1351991 reaction equation
[CH3:1][C:2]1[C:3]([N+:10]([O-])=O)=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[O:13]1CC[CH2:15][CH2:14]1.C(OC(=O)C)(=O)C>C(O)C.[Pd].C(OCC)(=O)C>[CH3:9][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH:10][C:14](=[O:13])[CH3:15]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 792913-Methyl-2-nitroanisole

Product 1

HCID 578995N-(2-Methoxy-6-methylphenyl)acetamideYield 87%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-methyl-2-nitroanisole (10.00 g, 59.8 mmol) in ethanol (60 mL)-tetrahydrofuran (60 mL) is added a 10% palladium on carbon (50% wet, 2.00 g), and the mixture is subjected to hydrogenation, and stirred at room temperature for 1.5 hour. After the reaction is completed, the reaction solution is filtered through celite, and the solvent is evaporated under reduced pressure. To a solution of the residue in ethyl acetate (110 ml) is added acetic anhydride (9.0 mL, 95.2 mmol), and the mixture is refluxed for 5 hours. The reaction solution is cooled with ice, and the precipitated solid is collected by filtration, and washed with hexane to give the title compound (9.28 g, yield: 87%).

Workup

  1. filtrationthe reaction solution is filtered through celite
  2. customthe solvent is evaporated under reduced pressure
  3. temperaturethe mixture is refluxed for 5 hours
  4. temperatureThe reaction solution is cooled with ice
  5. filtrationthe precipitated solid is collected by filtration
  6. washwashed with hexane

Sources & evidence

ORD record
ord-a8980aba367247a4b77abe9594e32bea
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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