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

HRID 887901

Reaction equation

HRID 887901 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([CH3:10])[CH:4]=1.CN(C)CC.[C:16](OC(=O)C)(=[O:18])[CH3:17]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:16](=[O:18])[CH3:17])=[C:5]([CH3:10])[CH:4]=1

Participants

5

Reactant 3

HCID 76102-Methyl-4-methoxyanilineHCID 7918Acetic AnhydrideHCID 11723Dimethylethylamine

Product 1

HCID 95082N-(4-Methoxy-2-methylphenyl)-acetamideYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

41.1 g (0.3 mol) of 4-methoxy-2-methylphenylamine and 37 g (0.5 mol) of dimethylethylamine were dissolved in 50 ml of tetrahydrofuran, and 35.7 g (0.35 mol) of acetic anhydride were added while stirring. The solution heated to boiling during this. It was stirred at room temperature for 1 hour and cooled to 0° C. The resulting precipitate was filtered off with suction and washed several times with a little cold tetrahydrofuran and dried. 40 g (75%) of colorless crystals of the desired product were obtained.

Workup

  1. temperatureThe solution heated
  2. stirringIt was stirred at room temperature for 1 hour
  3. filtrationThe resulting precipitate was filtered off with suction
  4. washwashed several times with a little cold tetrahydrofuran
  5. customdried

Sources & evidence

ORD record
ord-79359b97dd9445d7817107dff3c837b9
Source dataset
uspto-grants-2012_08
Patent number
US08247452B2

Linked notes

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