Pyridine → N-(5-Methoxy-2-methylphenyl)alpha-methylcinnamamide

HRID 1900806Notes

Reaction equation

HRID 1900806 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH3:10].N1C=CC=CC=1.[CH3:17][C:18](=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:19](Cl)=[O:20]>CC(C)=O>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]([CH3:10])=[C:2]([NH:1][C:19](=[O:20])[C:18]([CH3:17])=[CH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 995005-Methoxy-o-toluidineHCID 230201alpha-Methylcinnamoylchloride

Product 1

HCID 54285619N-(5-Methoxy-2-methylphenyl)alpha-methylcinnamamideYield 84.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Amino-4-methoxytoluene (13.2 g, 89.7 mmol) and pyridine (10 ml) were dissolved in acetone (112 ml), to which α-methylcinnamoylchloride (19.4 g, 107.6 mmol) was added while cooling and stirring. The mixture was stirred overnight at room temperature. The solvent was evaporated, and the residue was dissolved in chloroform, washed with water, dried, and condensed. The residue was purified by alumina chromatography (chloroform), and subjected to recrystallization with chloroform--n-hexane to obtain 21.27 g of the title compound as colorless crystals (84.4%).

Workup

  1. additionwas added
  2. temperaturewhile cooling
  3. stirringThe mixture was stirred overnight at room temperature
  4. customThe solvent was evaporated
  5. dissolutionthe residue was dissolved in chloroform
  6. washwashed with water
  7. customdried
  8. customcondensed
  9. customThe residue was purified by alumina chromatography (chloroform)
  10. customsubjected to recrystallization with chloroform

Sources & evidence

ORD record
ord-8ab1c8bf5b554bf792b66e36517bfddb
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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