Acetic Acid → 2,3-dimethoxy-6,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 2184450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2184450
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH2:11][N:12]2[CH:16]=[CH:15][CH:14]=[C:13]2[CH:17]=O)=[C:5]([N+:19]([O-])=O)[CH:4]=1.C(O)(=O)C.S([O-])([O-])(=O)=O.[Mg+2]>[Pd].C(OCC)(=O)C>[CH3:10][O:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[NH:19][CH2:17][C:13]3=[CH:14][CH:15]=[CH:16][N:12]3[CH2:11][C:6]=2[CH:7]=1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 3108271-[(4,5-Dimethoxy-2-nitrophenyl)methyl]-1H-pyrrole-2-carboxaldehyde

Produkt 1

HCID 3108382,3-dimethoxy-6,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepineAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of the 1-[(4,5-dimethoxy-2-nitrophenyl)methyl]-1H-pyrrole-2-carboxaldehyde of Step A (4.97 g), acetic acid (0.5 mL), magnesium sulfate (0.5 g) and 10% palladium on charcoal (0.5 g) in ethyl acetate (50 mL) was hydrogenated overnight at atmospheric pressure. The reaction was then filtered through Celite and the solvent removed in vacuo to give the crude title compound as an amber foam (3.2 g) which was used in the next step without further purification.

Aufarbeitung

  1. filtrationThe reaction was then filtered through Celite
  2. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ac25daea2ff54d8e94baf4a8f6141629
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900200B2

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