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Hydrochloric Acid → 8-Chloro-7-methoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline

HRID 1089808
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1089808
C([N:8]1[CH2:17][CH:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)[C:15]2[C:10](=[C:11]([Cl:30])[C:12]([O:28][CH3:29])=[CH:13][CH:14]=2)[CH2:9]1)C1C=CC=CC=1.Cl>C(O)C.[C].[Pd]>[Cl:30][C:11]1[C:12]([O:28][CH3:29])=[CH:13][CH:14]=[C:15]2[C:10]=1[CH2:9][NH:8][CH2:17][CH:16]2[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1
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Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 107884262-Benzyl-8-chloro-7-methoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 106166778-Chloro-7-methoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinolineAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

1.13 g of 2-benzyl-8-chloro-7-methoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline was dissolved in 28 ml of ethanol, and after adding thereto 0.22 ml of 12N hydrochloric acid, hydrogenation reaction was performed by addition of 0.1 g of 10% palladium-carbon. After the hydrogenation reaction was over, the reaction solution was filtered, and concentrated. The residue was dissolved in chloroform, washed with saturated aqueous sodium hydrogen carbonate solution and water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was recrystallized from ethyl acetate-n-hexane, giving 580 mg of 8-chloro-7-methoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline (m.p. 130°-132° C.). ##STR59##

Aufarbeitung

  1. additionafter adding
  2. customAfter the hydrogenation reaction
  3. filtrationwas filtered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in chloroform
  6. washwashed with saturated aqueous sodium hydrogen carbonate solution and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was recrystallized from ethyl acetate-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-25690b0bd77a4650b43b091eff2b9e11
Quelldatensatz
uspto-grants-1992_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05079256

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