1,8-Diazabicyclo(5.4.0)undec-7-ene → 7,8-dihydro-3-nitro-6H-cyclopenta[g]quinoline

HRID 36930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 36930
ClC1C=CC=CC=1[C:4]([C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH2:11][CH2:12]2)=[CH:8][C:7]=1[NH:15][CH:16]=[CH:17][N+:18]([O-:20])=[O:19])=O.C1CCN2C(=NCCC2)CC1>C1C=CC=CC=1>[N+:18]([C:17]1[CH:16]=[N:15][C:7]2[C:6]([CH:4]=1)=[CH:14][C:13]1[CH2:12][CH2:11][CH2:10][C:9]=1[CH:8]=2)([O-:20])=[O:19]

Komponenten

4

Edukt 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 677827716-(2-Chlorobenzoyl)-5-(2-nitroethenylamino)indan

Produkt 1

HCID 867486777,8-dihydro-3-nitro-6H-cyclopenta[g]quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

6-(2-Chlorobenzoyl)-5-(2-nitroethenylamino)indan (4.8 g) was added in small portions to a solution of DBU (4.8 g) in benzene (50 ml) with heating at 90° C. The mixture was refluxed for 30 minutes and, then, washed with 2N HCl and water and dried (MgSO4). The solvent was then distilled off to give crystals of 4-2-chlorophenyl)-7,8-dihydro-3-nitro-6H -cyclopenta[g]quinoline. The crystals were collected by filtration and washed with methanol (4.50 g, 99.1%). Recrystallization from ethanol gave light brown prisms, mp. 175°-176° C.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 30 minutes
  2. washwashed with 2N HCl and water
  3. dry with materialdried (MgSO4)
  4. distillationThe solvent was then distilled off

Quellen und Nachweise

ORD-Eintrag
ord-f4f7f8af08964c71ac06daedd7fb8b15
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418239

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