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Hydrochloric Acid → 6-hydroxy-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester

HRID 1833156
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1833156
[CH2:1]([O:3][C:4](=[O:25])[N:5]([C:16]1[CH:21]=[CH:20][C:19](O)=[C:18]([O:23][CH3:24])[CH:17]=1)[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14]C)[CH:9]=1)[CH3:2].Cl.[C:27](OCC)(=[O:29])C.[CH3:33][CH2:34]CCCC>CC(C)=O.O>[CH2:1]([O:3][C:4]([N:5]1[CH:6]=[CH:7][C:8]2[C:13](=[CH:12][C:11]([O:29][CH3:27])=[C:10]([OH:14])[CH:9]=2)[CH:16]1[CH2:21][C:20]1[CH:34]=[CH:33][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=1)=[O:25])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 21226206Ethyl acetate hexaneHCID 867601154-Hydroxy-3-methoxy-phenyl-2-(3-methoxy-phenyl)-ethyl-carbamic acid ethyl ester

Produkt 1

HCID 210349376-hydroxy-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl esterAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180
Acetone
Lösungsmittel
HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of (2,2-dimethoxy-ethyl)-[1-(4-hydroxy-3-methoxy-phenyl-2-(3-methoxy-phenyl)-ethyl-carbamic acid ethyl ester (3.7 g, 8.55 mmol) in acetone (150 mL) was added 6N hydrochloric acid (38 mL) at 0° C. The reaction mixture was stirred at room temperature for 15 hrs. The mixture was diluted with water. The solvent was evaporated and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with saturated aqueous sodium chloride solution (80 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 50% ethyl acetate/hexane) afforded 6-hydroxy-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester (1.17, 37% yield) as a colorless oil.

Aufarbeitung

  1. customThe solvent was evaporated
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
  3. washThe combined extracts were washed with saturated aqueous sodium chloride solution (80 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7b1cb67951c9470ba915dd69998121ae
Quelldatensatz
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07067529B2

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