2-Chloro-5-(4-nitrobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine → 2-Chloro-5-(4-aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine

HRID 962512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 962512
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([C:15](=[O:25])[C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][C:4]=2[CH:3]=1.[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([C:15](=[O:25])[C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)[CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][C:4]=2[CH:3]=1

Komponenten

5

Edukt 2

HCID 539356852-Chloro-5-(4-nitrobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 544045372-Chloro-5-(4-aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepineAusbeute 73,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 21584252Ethanol ethylacetateLösungsmittel

Versuchsvorschrift

A solution of 2.1 g of 2-chloro-5-(4-nitrobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine in 400 ml of ethyl acetate-ethanol (1:1) and 0.25 g of palladium-on-carbon is hydrogenated in a Parr hydrogenator under 38 pounds per square inch of hydrogen. The mixture is filtered through diatomaceous earth and the filtrate concentrated to dryness. The solid (1.94 g) is dissolved in dichloromethane and the solution filtered through a thin pad of hydrous magnesium silicate. The filter pad is washed with dichloromethane and the filtrate concentrated. The residue is crystallized from dichloromethane-hexane to give 1.43 g of crystals, m.p. 211°-214° C.

Aufarbeitung

  1. filtrationThe mixture is filtered through diatomaceous earth
  2. concentrationthe filtrate concentrated to dryness
  3. dissolutionThe solid (1.94 g) is dissolved in dichloromethane
  4. filtrationthe solution filtered through a thin pad of hydrous magnesium silicate
  5. washThe filter pad is washed with dichloromethane
  6. concentrationthe filtrate concentrated
  7. customThe residue is crystallized from dichloromethane-hexane

Quellen und Nachweise

ORD-Eintrag
ord-3198682b2514423fba3b40da4e343bf1
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05760031

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