Benzene → (Z)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4,5-trimethoxybenzeneacetyl)-1-[(3,4,5-trimethoxyphenyl)methylene]isoquinoline

HRID 597243

Reaktionsgleichung

Reaktionsgleichung von HRID 597243
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][C:14]([OH:16])=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C1C=CC=CC=1.C(N(CC)C#CC)C.[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][C:42]=1[O:43][CH3:44])[C:39](=[CH:45][C:46]1[CH:51]=[C:50]([O:52][CH3:53])[C:49]([O:54][CH3:55])=[C:48]([O:56][CH3:57])[CH:47]=1)[NH:38][CH2:37][CH2:36]2>N1C=CC=CC=1>[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][C:42]=1[O:43][CH3:44])/[C:39](=[CH:45]/[C:46]1[CH:51]=[C:50]([O:52][CH3:53])[C:49]([O:54][CH3:55])=[C:48]([O:56][CH3:57])[CH:47]=1)/[N:38]([C:14](=[O:16])[CH2:13][C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:37][CH2:36]2

Komponenten

6

Edukt 4

HCID 241BenzeneHCID 703723,4,5-Trimethoxyphenylacetic acidHCID 77909N,N-Diethyl-1-propyn-1-amineHCID 706389523,4-Dihydro-6,7-dimethoxy-1-[(3,4,5-trimethoxyphenyl)methylene]isoquinoline

Produkt 1

HCID 21447095(Z)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4,5-trimethoxybenzeneacetyl)-1-[(3,4,5-trimethoxyphenyl)methylene]isoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a suspension of 24 parts of 3,4,5-trimethoxybenzeneacetic acid in 25 parts of benzene is added 7 parts of N,N-diethyl-1-propyne-1-amine, followed by a solution of 12 parts of 3,4-dihydro-6,7-dimethoxy-1-[(3,4,5-trimethoxyphenyl)methylene]isoquinoline [Ber. deut. chem. Ges., 55, 2989 (1922)] in 60 parts of pyridine. The resultant mixture is stirred at room temperatures for 18 hours, whereupon it is consecutively washed with aqueous 5% potassium carbonate, approximately 0.2% hydrochloric acid, and water, then dried over anhydrous sodium sulfate and stripped of solvent by vacuum distillation. The residue, crystallized from methanol, affords (Z)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4,5-trimethoxybenzeneacetyl)-1-[(3,4,5-trimethoxyphenyl)methylene]isoquinoline melting at 148°-150°.

Aufarbeitung

  1. washis consecutively washed with aqueous 5% potassium carbonate, approximately 0.2% hydrochloric acid, and water
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationstripped of solvent by vacuum distillation
  4. customThe residue, crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-ea47d3b3a836499cb50a1aec2aec07a0
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04013666

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