Dimethylformamide → 5,6-Dihydro-3-methoxy-8-[3-(2-methyl-1,3-dioxocyclopent-2-yl)prop-1-en-2-yl]isoquinoline

HRID 972516

Reaktionsgleichung

Reaktionsgleichung von HRID 972516
[CH3:1][CH:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].CN(C)C=O.[I-].C[N+](C)(C)[CH2:17][C:18]([C:20]1[C:29]2[CH:28]=[N:27][C:26]([O:30][CH3:31])=[CH:25][C:24]=2[CH2:23][CH2:22][CH:21]=1)=[CH2:19]>C(N(CC)CC)C>[CH3:31][O:30][C:26]1[N:27]=[CH:28][C:29]2[C:20]([C:18]([CH2:17][C:2]3([CH3:1])[C:6](=[O:7])[CH2:5][CH2:4][C:3]3=[O:8])=[CH2:19])=[CH:21][CH2:22][CH2:23][C:24]=2[CH:25]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 130052-Methyl-1,3-cyclopentanedioneHCID 21404775N,N,N-trimethyl-N-(2-[5,6-dihydro-3-methoxyisoquinol-8-yl]prop-2-en-1-yl)ammonium iodide

Produkt 1

HCID 214047775,6-Dihydro-3-methoxy-8-[3-(2-methyl-1,3-dioxocyclopent-2-yl)prop-1-en-2-yl]isoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A solution containing 0.75 part of 2-methylcyclopentane-1,3-dione in 19 parts of dimethylformamide is treated sequentially with 1.0 part by volume of triethylamine and 1.9 parts of N,N,N-trimethyl-N-(2-[5,6-dihydro-3-methoxyisoquinol-8-yl]prop-2-en-1-yl)ammonium iodide. The resulting homogeneous solution is heated at about 135° for 43/4 hours. It is allowed to cool to room temperature and solvent is removed under reduced pressure. The remaining material is diluted with water-ether and enough 5% sodium hydroxide solution is added to bring the pH to 10. The aqueous and organic layers are separated and the aqueous layer is extracted with ether. The extracts are washed sequentially with 5% sodium hydroxide solution, 2.5% aqueous formic acid and saturated sodium chloride solution, then dried over anhydrous sodium sulfate. Upon solvent removal, an oil remains which is taken into ether. Then n-hexane is added until the solution becomes turbid. Charcoal is added and the mixture is filtered. Solvent is removed under reduced pressure to yield an oil which crystallizes upon standing. Recrystallization from acetone-water gives pure 5,6-dihydro-3-methoxy-8-[3-(2-methyl-1,3-dioxocyclopent-2-yl)prop-1-en-2-yl]isoquinoline, which is identical to the product obtained in Example 18A.

Aufarbeitung

  1. temperatureThe resulting homogeneous solution is heated at about 135° for 43/4 hours
  2. customsolvent is removed under reduced pressure
  3. additionThe remaining material is diluted with water-ether and enough 5% sodium hydroxide solution
  4. additionis added
  5. customThe aqueous and organic layers are separated
  6. extractionthe aqueous layer is extracted with ether
  7. washThe extracts are washed sequentially with 5% sodium hydroxide solution, 2.5% aqueous formic acid and saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. customUpon solvent removal
  10. additionThen n-hexane is added until the solution
  11. additionCharcoal is added
  12. filtrationthe mixture is filtered
  13. customSolvent is removed under reduced pressure
  14. customto yield an oil which
  15. customcrystallizes
  16. customRecrystallization from acetone-water

Quellen und Nachweise

ORD-Eintrag
ord-7908cddc9d514f3b83aff449312458c6
Quelldatensatz
uspto-grants-1977_10
Patentnummer
US04053476

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