N-(2-nitrobenzoyl)pyrrole-2-carboxaldehyde → 10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

HRID 440734

Reaktionsgleichung

Reaktionsgleichung von HRID 440734
[N+:1]([C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]=O)=[O:7])([O-])=O>C(OCC)(=O)C.Cl.[Pd]>[CH:10]1[CH:11]=[CH:12][N:8]2[C:6](=[O:7])[C:5]3[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=3[NH:1][CH2:13][C:9]=12

Komponenten

5

Edukt 1

HCID 21837074N-(2-nitrobenzoyl)pyrrole-2-carboxaldehyde

Produkt 1

HCID 2183707610,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-oneAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1.5 g of N-(2-nitrobenzoyl)pyrrole-2-carboxaldehyde in 50 ml of ethyl acetate, 2 drops of concentrated HCl and 0.3 g of 10% Pd/C is shaken in a Parr apparatus under hydrogen pressure for 2 hours. The reaction mixture is filtered through diatomaceous earth and the filtrate concentrated in vacuo to give 1.0 g of a yellow oil. The residue is purified on thick layer chromatography plates by elution with 4:1 ethyl acetate:hexane to give 107 mg of the desired product as an oily solid.

Aufarbeitung

  1. filtrationThe reaction mixture is filtered through diatomaceous earth
  2. concentrationthe filtrate concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e45397ec377345c5a086fe198ad08c58
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05521173

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