2-Methyl-4-methoxyaniline → N-(4-Methoxy-2-methylphenyl)-acetamide

HRID 1014402Notes

Reaction equation

HRID 1014402 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:11](OC(=O)C)(=[O:13])[CH3:12]>C(O)(=O)C>[CH3:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:3]=1[NH:4][C:11](=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 76102-Methyl-4-methoxyanilineHCID 7918Acetic Anhydride

Product 1

HCID 95082N-(4-Methoxy-2-methylphenyl)-acetamideYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

2-methyl-4-(methyloxy)aniline (5 ml, 39 mmol) was dissolved in acetic acid (40 ml) and acetic anhydride (3.7 ml, 39 mmol) was added dropwise. Reaction was heated to 60° C. After 30 min, most of the solvent was removed under reduced pressure and the residue diluted with EtOAc. A saturated solution of sodium bicarbonate was added until solution was pH 8. Organics were then washed with water and a saturated brine solution and dried over sodium sulfate. Solvents were removed under reduced pressure to afford N-[2-methyl-4-(methyloxy)phenyl]acetamide (6.37 g, 35.5 mmol) as a pink fluffy solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.95-2.06 (m, 3 H) 2.14 (s, 3 H) 3.71 (s, 3 H) 6.70 (dd, J=8.71, 2.84 Hz, 1 H) 6.77 (d, J=2.75 Hz, 1 H) 7.18 (d, J=8.61 Hz, 1 H) 9.16 (s, 1 H)

Workup

  1. customReaction
  2. custommost of the solvent was removed under reduced pressure
  3. additionthe residue diluted with EtOAc
  4. additionA saturated solution of sodium bicarbonate was added until solution
  5. washOrganics were then washed with water
  6. dry with materiala saturated brine solution and dried over sodium sulfate
  7. customSolvents were removed under reduced pressure

Sources & evidence

ORD record
ord-ed0a162fec5f445787f0fab1fb77b111
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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