Hydrochloric Acid → Hydrochloric Acid

HRID 2272009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2272009
[N+:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[N:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)([O-])=O.[ClH:17]>[Pd].O=[Pt]=O.CO>[NH:9]1[CH2:10][CH2:11][CH2:12][C@@H:13]2[C:14]3[CH:15]=[CH:16][C:4]([NH2:1])=[CH:5][C:6]=3[CH2:7][C@H:8]12.[ClH:17]

Komponenten

7

Edukt 2

HCID 313Hydrochloric AcidHCID 126342947-nitro-9H-indeno[2,1-b]pyridine

Produkt 2

HCID 313Hydrochloric AcidHCID 58294569cis-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridin-7-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 345198Adams' catalystKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 7-nitro-9H-indeno[2,1-b]pyridine (3.25 g), 10% palladium on carbon (0.35 g), and methanol (50 mL) is shaken under hydrogen atmosphere (3 bar) at room temperature for 22 h. PtO2 (0.50 g) and 4 M aqueous hydrochloric acid (3.2 mL) are then added and shaking is continued under hydrogen atmosphere (1 bar) at room temperature for another 22 h. The catalysts are separated by filtration and the filtrate is concentrated to give the crude title compound as its hydrochloric acid salt that is used without further purification or transformed to the free base by treatment with aqueous NaOH solution and extraction into ethyl acetate. Yield: 4.20 g (ca. 80% pure); LC (method 1): tR=0.52 min; Mass spectrum (ESI+): m/z=189 [M+H]+.

Aufarbeitung

  1. stirringshaking
  2. customat room temperature
  3. customfor another 22 h
  4. customThe catalysts are separated by filtration
  5. concentrationthe filtrate is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-2b6e08952c0742bb9e8f7531567e64be
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120769B2

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