Hydrochloric Acid → Hydrochloric Acid

HRID 521016Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 521016
[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-3ea8d5ca11ed41b296736aab7e4919c6
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328072B2

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