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

HRID 596822

反応式

HRID 596822 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

A solution containing 0.75 parts 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 4 3/4 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 9 A.

後処理

  1. temperatureThe resulting homogeneous solution is heated at about 135° for 4 3/4 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

出典と根拠

ORDレコード
ord-f22deb9e674e4bd7b3d192a552f38ce6
出典データセット
uspto-grants-1977_03
特許番号
US04012391

関連ノート

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