6-Ethoxycarbonylamino-1-methyl-3,4-dihydroisoquinoline → 6-Ethoxycarbonylamino-1-methylisoquinoline

HRID 1173129Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1173129
[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([CH3:17])=[N:12][CH2:11][CH2:10]2)=[O:5])[CH3:2]>[C].[Pd].CC1C=CC(C(C)C)=CC=1>[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([CH3:17])=[N:12][CH:11]=[CH:10]2)=[O:5])[CH3:2]

Komponenten

4

Edukt 1

HCID 226741196-Ethoxycarbonylamino-1-methyl-3,4-dihydroisoquinoline

Produkt 1

HCID 226741466-Ethoxycarbonylamino-1-methylisoquinolineAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 7463P-CymeneLösungsmittel

Reaktionsbedingungen

Temperatur
195 °C

Versuchsvorschrift

p-Cymene (100 ml) and palladium carbon (0.9 g) were added to 6-ethoxycarbonylamino-1-methyl-3,4-dihydroisoquinoline, followed by heating under stirring at 195° C. for one hour in a nitrogen atmosphere. The catalyst was filtered off and washed with ethanol, and then the filtrate was partially evaporated. After extracting with 1N hydrochloric acid, the extract was basified with potassium carbonate and then extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate anhydride. The solvent was evaporated, to give the title compound (0.629 g, 69%, 2 steps) as pale yellow crystals.

Aufarbeitung

  1. temperatureby heating
  2. filtrationThe catalyst was filtered off
  3. washwashed with ethanol
  4. customthe filtrate was partially evaporated
  5. extractionAfter extracting with 1N hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate anhydride
  9. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-fcfe666d5bc0439eb79fc1e8b0f2baf6
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834049B2

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