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Sulfuric Acid → 4-(6-Fluoro-3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 1768815
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1768815
[CH3:1][O:2][C:3]1[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[CH:21][C:4]=1[CH2:5][NH:6][CH2:7][CH:8](O)[C:9]1[C:14]([F:15])=[CH:13][C:12]([O:16][CH3:17])=[C:11]([O:18][CH3:19])[CH:10]=1.S(=O)(=O)(O)O.C([O-])(=O)C.[Na+]>FC(F)(F)C(O)=O>[F:15][C:14]1[C:9]([CH:8]2[C:21]3[C:4](=[C:3]([O:2][CH3:1])[C:24]([O:25][CH3:26])=[CH:23][CH:22]=3)[CH2:5][NH:6][CH2:7]2)=[CH:10][C:11]([O:18][CH3:19])=[C:12]([O:16][CH3:17])[CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 517045Sodium AcetateHCID 14719568alpha-[[(2,3-Dimethoxybenzyl)amino]methyl]-6-fluoro-3,4-dimethoxybenzyl alcohol

Produkt 1

HCID 199597004-(6-Fluoro-3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinolineAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422
Trifluoroacetic acid
Lösungsmittel

Versuchsvorschrift

α-[[(2,3-dimethoxybenzyl)amino]methyl]-6-fluoro-3,4-dimethoxybenzyl alcohol (1.0 g) was dissolved in 7 ml of trifluoroacetic acid, and after adding thereto under ice cooling, conc. sulfuric acid (0.25 ml), the mixture was stirred for 40 minutes. 0.72 g of sodium acetate was added to the reaction mixture, and the mixture was concentrated. To the residue was added chloroform and water, and the mixture was basified by addition of conc. aqueous ammonia under ice cooling. After separating procedure, the chloroform layter was collected, washed with saturated aqueous NaCl solution, and drioed over anhydrous sodium sulfate. The solvent was distilled off, 0.94 g of 4-(6-fluoro-3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline was obtained as a syrupy matter.

Aufarbeitung

  1. additionafter adding
  2. concentrationthe mixture was concentrated
  3. additionTo the residue was added chloroform and water
  4. additionthe mixture was basified by addition of conc. aqueous ammonia under ice cooling
  5. customAfter separating procedure
  6. customthe chloroform layter was collected
  7. washwashed with saturated aqueous NaCl solution
  8. distillationThe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-b895a860d7a6413cabd8322a7b2463d2
Quelldatensatz
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05378849

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