Acetic Anhydride → Acetamide, N-(3-methoxyphenyl)-

HRID 475930Notes

Reaction equation

HRID 475930 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[C:10](OC(=O)C)(=[O:12])[CH3:11]>O1CCCC1>[CH3:11][C:10]([NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:12]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 108243-Methoxyaniline

Product 1

HCID 11494Acetamide, N-(3-methoxyphenyl)-Yield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Methoxyaniline 12 (5 gm, 0.041 moles) was dissolved in 30 ml tetrahydrofuran (THF) at room temperature under argon. Acetic anhydride (5.8 ml, 0.061 moles) was added. After stirring for 2 hours, the mixture was evaporated under reduced pressure, dissolved in several mls of toluene and purified by flash chromatography on silica gel, eluting with a mixture of ethyl acetate and hexane. 3-Methoxyacetanilide 13 (6.63 gm, 99% yield) was isolated after removing the solvent. 1H NMR (CDCl3) δ 7.6, 1H, br; 7.2, 2H, m; 6.95, 1H, d; 6.66, 1H, d; 3.78, 3H, s; 2.16, 3H, s.

Workup

  1. customthe mixture was evaporated under reduced pressure
  2. dissolutiondissolved in several mls of toluene
  3. custompurified by flash chromatography on silica gel
  4. washeluting with a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-be92259c6ef0444e98cadd192b9455d5
Source dataset
uspto-grants-2014_01
Patent number
US08637658B2

Reaction notes

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