7-(Azidomethyl)quinoline → Quinolin-7-ylmethanamine

HRID 657771

Reaktionsgleichung

Reaktionsgleichung von HRID 657771
[N:1]([CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1)=[N+]=[N-]>[Ni].CO>[N:12]1[C:13]2[C:8](=[CH:7][CH:6]=[C:5]([CH2:4][NH2:1])[CH:14]=2)[CH:9]=[CH:10][CH:11]=1

Komponenten

4

Edukt 1

HCID 598406937-(Azidomethyl)quinoline

Produkt 1

HCID 17904490Quinolin-7-ylmethanamineAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

7-(Azidomethyl)quinoline (1.1 g, 5.7 mmol) was hydrogenated (1 atm) in the presence of Raney nickel (1.5 g, 26 mmol) in methanol (30 mL) until completion of the reaction. Catalyst was filtered off and the filtrate was concentrated under reduced pressure to a yellow oil which was dissolved in EtOAc (32 mL) and extracted with 1N hydrochloric acid (3×32 mL). The combined acidic aqueous phases were adjust to pH˜10 with 1N sodium hydroxide solution, and extracted with EtOAc (3×35 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to afford a white solid (0.89 g, 94%).

Aufarbeitung

  1. customuntil completion of the reaction
  2. filtrationCatalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure to a yellow oil which
  4. dissolutionwas dissolved in EtOAc (32 mL)
  5. extractionextracted with 1N hydrochloric acid (3×32 mL)
  6. extractionextracted with EtOAc (3×35 mL)
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-12c48e6fd3ec4232afc27eb37e2f6f68
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076345B2

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