4-Pyridinecarboxaldehyde → 3-(Pyridin-4-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

HRID 1730154Notes

Reaction equation

HRID 1730154 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=[O:15])[CH3:14])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH:16](=O)[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.[OH-].[Na+]>O>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13](=[O:15])[CH:14]=[CH:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 143453',4',5'-TrimethoxyacetophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 540288583-(Pyridin-4-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

44 G. of 3',4',5'-trimethoxyacetophenone and 440 ml. of water are heated at 70° C. with stirring and treated with 20.2 ml. of isonicotinaldehyde. Then, there are added, three times at intervals of 30 minutes, 4 ml. each time of a 6% sodium hydroxide solution in water/methaol (2:1). The resulting reaction mixture is kept overnight at 70° C., cooled in an ice-bath and the resulting crystals are filtered off then washed with ethanol and ether to result in a product with a melting point at 124°-127° C. After recrystallization from methanol/ether there are obtained crystals of melting ppont 128°-130° C. The mother liquors are evaporated under reduced pressure, taken up in ethyl acetic and the organic phase is washed twice with water. The washings are extracted twice with ethyl acetate and the combined organic phases dried over sodium sulfate and evaporated under reduced pressure. The residue is chromatographed on a 30-fold amount of silica gel (ether/diethylamine 95:5) and after recrystallization from ethanol/ether, there are obtained 3',4',5'-trimethoxy-3-(4-pyridyl)-acrylophenone of melting point 127°-129° C.

Workup

  1. additiontreated with 20.2 ml
  2. additionThen, there are added
  3. customat intervals of 30 minutes, 4 ml
  4. customThe resulting reaction mixture
  5. temperaturecooled in an ice-bath
  6. filtrationthe resulting crystals are filtered off
  7. washthen washed with ethanol and ether
  8. customto result in a product with a melting point at 124°-127° C
  9. customAfter recrystallization from methanol/ether there
  10. customare obtained crystals
  11. customof melting ppont 128°-130° C
  12. customThe mother liquors are evaporated under reduced pressure
  13. washthe organic phase is washed twice with water
  14. extractionThe washings are extracted twice with ethyl acetate
  15. dry with materialthe combined organic phases dried over sodium sulfate
  16. customevaporated under reduced pressure
  17. customThe residue is chromatographed on a 30-fold amount of silica gel (ether/diethylamine 95:5)
  18. customafter recrystallization from ethanol/ether, there

Sources & evidence

ORD record
ord-cc7c79c477ee4576a1a9d5df7ab9d027
Source dataset
uspto-grants-1976_11
Patent number
US03991197

Reaction notes

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