6-Chloroquinoline-2-carbaldehydeoxime → (6-Chloroquinolin-2-yl)methanamine

HRID 2053810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2053810
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH:12]=[N:13]O)[CH:6]=[CH:5]2.[H][H]>CO.O1CCCC1.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][NH2:13])[CH:6]=[CH:5]2

Komponenten

6

Edukt 2

HCID 1363477776-Chloroquinoline-2-carbaldehydeoximeHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 69312377(6-Chloroquinolin-2-yl)methanamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 0.78 g (3.79 mmol) of 6-chloroquinoline-2-carbaldehydeoxime in 30 mL of saturated ammoniacal methanol and 10 mL of tetrahydrofuran is hydrogenated with Raney nickel for 48 hours at 3 bar hydrogen pressure. The catalyst is filtered off and the solution is concentrated. The residue is chromatographed on silica gel, eluting with a gradient of dichloromethane/methanol (90:10) to dichloromethane/methanol/25% aqueous ammonia (90:10:1). The corresponding fractions are combined and concentrated by evaporation. Yield: 0.33 g (45% of theory); Rf value: 0.43 (silica gel; dichloromethane/methanol=9:1); C10H9ClN2 (192.65); mass spectrum: (M+H)+=193/195 (chlorine isotope).

Aufarbeitung

  1. filtrationThe catalyst is filtered off
  2. concentrationthe solution is concentrated
  3. customThe residue is chromatographed on silica gel
  4. washeluting with a gradient of dichloromethane/methanol (90:10) to dichloromethane/methanol/25% aqueous ammonia (90:10:1)
  5. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-beffb6d93cf947278da9a19422a589d6
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326791B2

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