Pyridine → 3,4,5-Trimethoxybenzeneacetyl-1-[(3,4-dimethoxyphenyl)-methylene]isoquinoline

HRID 597242

Reaktionsgleichung

Reaktionsgleichung von HRID 597242
CO[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1OC)[C:9](=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)[NH:8][CH2:7][CH2:6]2.N1C=CC=CC=1.C(N(C(C)C)C(C)C)C.[CH3:41][O:42][C:43]1[CH:44]=[C:45]([CH2:53][C:54](Cl)=[O:55])[CH:46]=[C:47]([O:51][CH3:52])[C:48]=1[O:49][CH3:50]>C(Cl)(Cl)Cl.C1C=CC=CC=1>[CH3:52][O:51][C:47]1[CH:46]=[C:45]([CH2:53][C:54]([C:7]2[NH:8][C:9](=[CH:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=3)[C:10]3[C:5]([CH:6]=2)=[CH:4][CH:3]=[CH:12][CH:11]=3)=[O:55])[CH:44]=[C:43]([O:42][CH3:41])[C:48]=1[O:49][CH3:50]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 81531DiisopropylethylamineHCID 110321242-(3,4,5-trimethoxyphenyl)acetyl ChlorideHCID 681233913,4-Dihydro-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methylene]isoquinoline

Produkt 1

HCID 867345733,4,5-Trimethoxybenzeneacetyl-1-[(3,4-dimethoxyphenyl)-methylene]isoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a suspension of 12 parts of 3,4-dihydro-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methylene]isoquinoline in 50 parts of pyridine and 5 parts of N-ethyl-N-(1-methylethyl)-2-propanamine is added a solution of 10 parts of 3,4,5-trimethoxybenzeneacetyl chloride in 45 parts of benzene. The resultant mixture is heated at the boiling point under reflux for 1 hour, then cooled and thereupon diluted with 500 parts of chloroform. The resultant solution is washed with water, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation. The residue is crystallized from a mixture of ethyl acetate and ether to give (Z)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4,5-trimethoxybenzeneacetyl-1-[(3,4-dimethoxyphenyl)-methylene]isoquinoline melting at 164°-170°.

Aufarbeitung

  1. temperatureunder reflux for 1 hour
  2. temperaturecooled
  3. washThe resultant solution is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationstripped of solvent by vacuum distillation
  6. customThe residue is crystallized from a mixture of ethyl acetate and ether

Quellen und Nachweise

ORD-Eintrag
ord-9277f6817e6345548df65511f3cdca40
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04013666

Verknüpfte Notizen

Wird geladen…