Methyl iodide → 3-Acetyl-4-methoxyacetanilide

HRID 1870230Notes

Reaction equation

HRID 1870230 reaction equation
CI.[C:3]([C:6]1[CH:7]=[C:8]([NH:13][C:14](=[O:16])[CH3:15])[CH:9]=[CH:10][C:11]=1[OH:12])(=[O:5])[CH3:4].[C:17](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:3]([C:6]1[CH:7]=[C:8]([NH:13][C:14](=[O:16])[CH3:15])[CH:9]=[CH:10][C:11]=1[O:12][CH3:17])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 81720N-(3-Acetyl-4-hydroxyphenyl)acetamide

Product 1

HCID 28174183-Acetyl-4-methoxyacetanilideYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (3.42 ml, 7.81 g, 55 mmol) was added to a stirred mixture of N-(3-acetyl-4-hydroxyphenyl)acetamide (J.Org.Chem. 1995, 60, 4324-4330) (9.65 g, 50 mmol) and potassium carbonate (13.82 g, 100 mmol) in dimethylformamide (50 ml). The mixture was stirred at room temperature for 72 hours, then the solvent was evaporated under reduced pressure. Water (100 ml) was added and the mixture was extracted with ethyl acetate (6×100 ml). The combined organic fractions were dried (MgSO4) and evaporated under reduced pressure to give N-(3-acetyl-4-methoxyphenyl)acetamide as a tan solid (10.34 g, 100%), 1H NMR (d6 -DMSO) δ 9.91 (1H, br. s), 7.76 (2H, m), 7.12 (1H, d, J=9.6 Hz), 3.86 (3H, s), 2.52 (3H, s), and 2.01 (3H, s). m/e (CI+) 208 (MH+).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionWater (100 ml) was added
  3. extractionthe mixture was extracted with ethyl acetate (6×100 ml)
  4. dry with materialThe combined organic fractions were dried (MgSO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-968a67cf23a345b4b7bec1c6c7034b40
Source dataset
uspto-grants-2000_08
Patent number
US06096766

Reaction notes

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