Acetone → N-(2-methyl-4,5-dimethoxyphenyl)cinnamamide

HRID 1900871Notes

Reaction equation

HRID 1900871 reaction equation
[CH3:1][O:2][C:3]1[C:9]([O:10][CH3:11])=[CH:8][C:6]([NH2:7])=[C:5]([CH3:12])[CH:4]=1.N1C=CC=CC=1.CC(C)=O.[C:23](Cl)(=[O:32])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O>[CH3:12][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:9]([O:10][CH3:11])=[CH:8][C:6]=1[NH:7][C:23](=[O:32])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 1049PyridineHCID 660233-Phenylprop-2-enoyl chlorideHCID 2665854,5-Dimethoxy-2-methylaniline

Product 1

HCID 53987657N-(2-methyl-4,5-dimethoxyphenyl)cinnamamideYield 97.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4,5-dimethoxy-2-methylaniline (40.1 g), pyridine (48.5 ml), and acetone (350 ml), cinnamoyl chloride (44.0 g) was added dropwise at room temperature over 15 minutes. After allowing to react at room temperature for 2 hours, water (15 ml) was added and the mixture was stirred for 20 minutes. The solvent was distilled off under reduced pressure, and the residue was dissolved in chloroform, followed by washing with 1N HCl, 1N caustic soda and water in this order, and drying. Chloroform was evaporated. Precipitated crystals were collected by filtration with ether. 69.8 g of the title compound was obtained as yellow crystals (97.8%).

Workup

  1. customto react at room temperature for 2 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washby washing with 1N HCl, 1N caustic soda and water in this order
  5. customdrying
  6. customChloroform was evaporated
  7. customPrecipitated crystals
  8. filtrationwere collected by filtration with ether

Sources & evidence

ORD record
ord-fb28d69fdfc242a5bcd10c8088961451
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

Loading…