Ammonium Chloride → 7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine hydrochloride

HRID 1932355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1932355
[CH3:1][C:2]([Mg]Br)=[CH:3][CH3:4].[CH2:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][N:8]1[C:17]1[C:22]([N+:23]([O-])=O)=[CH:21][CH:20]=[CH:19][N:18]=1.[Cl-:26].[NH4+]>O1CCCC1>[ClH:26].[CH2:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][N:8]1[C:17]1[N:18]=[CH:19][CH:20]=[C:21]2[C:3]([CH3:4])=[C:2]([CH3:1])[NH:23][C:22]=12

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 9196247Isoquinoline, 1,2,3,4-tetrahydro-2-(3-nitro-2-pyridinyl)-HCID 178448414HCID 178448414, Verbindung

Produkt 1

HCID 671411697-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

1-Methyl-1-propenyl magnesium bromide (0.5M in tetrahydrofuran solution; 112 ml) was slowly added at −78° C. to a solution of 2-(1,2,3,4-tetrahydroisoquinolin-2-yl)-3-nitropyridine (4.8 g, 18.8 mmol) prepared in Preparation 20 in anhydrous tetrahydrofuran (150 ml). The reaction mixture was stirred for 4 hours at −20° C. 20% ammonium chloride solution was added to the reaction mixture, which was then extracted with ethyl acetate. The separated organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1, v/v). The resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered to give 1.3 g of the titled compound as yellow solid.

Aufarbeitung

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe separated organic layer was dried on anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1
  5. dissolutionThe resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-e9ad34702a4f42b0a2f5fa2570519dea
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188114B2

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