N-(3-Methylphenyl)acetamide → N-3,4-methylenedioxyphenyl-N-m-tolylamine

HRID 1976521Notes

Reaction equation

HRID 1976521 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:9]([CH3:11])=O)[CH:3]=1.[C:12](=[O:15])([O-])[O-:13].[K+].[K+].[OH-].[K+]>S([O-])([O-])(=O)=O.[Cu+2].CO>[CH2:12]1[O:15][C:3]2[CH:4]=[CH:11][C:9]([NH:8][C:4]3[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][CH:5]=3)=[CH:1][C:2]=2[O:13]1

Participants

6

Reactant 3

HCID 10843N-(3-Methylphenyl)acetamideHCID 11430Potassium CarbonateHCID 14797Potassium Hydroxide

Product 1

HCID 21998423N-3,4-methylenedioxyphenyl-N-m-tolylamineYield 40.3%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 887MethanolSolvent

Procedure

A mixture of 40.0 g (268.1 mol) of m-acetotoluidine, 45.0 g (223.9 mol) of 3,4-bromomethylenedioxybenzene, 8 g (50.1 mol) of copper sulfate, and 31 g (267.7 mmol) of potassium carbonate was reacted in the same manner as in Example 5 (2) to obtain a crude reaction product. A mixture of this crude product, 50 g (757.4 mmol) of 85% KOH, and 200 ml of methanol was refluxed overnight and then concentrated. Water was added thereto. The resultant mixture was extracted with toluene twice. The toluene phase was washed with water three times, dried, and then concentrated. The residue was distilled under vacuum to obtain 24.51 g of N-3,4-methylenedioxyphenyl-N-m-tolylamine.

Workup

  1. customto obtain a crude
  2. customreaction product
  3. temperaturewas refluxed overnight
  4. concentrationconcentrated
  5. additionWater was added
  6. extractionThe resultant mixture was extracted with toluene twice
  7. washThe toluene phase was washed with water three times
  8. customdried
  9. concentrationconcentrated
  10. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-e3718fc57c9e4add953c25593165c124
Source dataset
uspto-grants-2001_05
Patent number
US06228547B1

Reaction notes

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