2-Cyclopentene-1,4-dione → 9-(3-bromo-4-fluorophenyl)-5,6,7,9-tetrahydro-1H-cyclopenta[b]quinoline-1,8(4H)-dione

HRID 1058679

Reaktionsgleichung

Reaktionsgleichung von HRID 1058679
[C:1]1(=[O:7])[CH:5]=[CH:4][C:3](=O)[CH2:2]1.[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[F:17])[CH:12]=O.[NH2:18][C:19]1[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[CH:20]=1>C(O)C>[Br:8][C:9]1[CH:10]=[C:11]([CH:12]2[C:20]3[C:21](=[O:25])[CH2:22][CH2:23][CH2:24][C:19]=3[NH:18][C:3]3[CH:4]=[CH:5][C:1](=[O:7])[C:2]2=3)[CH:14]=[CH:15][C:16]=1[F:17]

Komponenten

5

Edukt 3

HCID 702582-Cyclopentene-1,4-dioneHCID 788923-Aminocyclohex-2-en-1-oneHCID 1736043-Bromo-4-fluorobenzaldehyde

Produkt 1

HCID 97996939-(3-bromo-4-fluorophenyl)-5,6,7,9-tetrahydro-1H-cyclopenta[b]quinoline-1,8(4H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 4-cyclopentene-1,3-dione (1.14 g, 10.2 mmol), 3-bromo-4-fluorobenzaldehyde (2.05 g, 10.1 mmol), and 3-amino-2-cyclohexenone (1.14 g, 10.2 mmol) in absolute ethanol (50 mL) were magnetically stirred and heated at reflux for 36 hours. The mixture was vacuum filtered and the solid was washed with ethyl acetate-hexane. The filtrate was concentrated and the residue was chromatographed on silica gel (100 g) using EtOAc-hexane (75:25), then EtOAc, finally EtOAc—EtOH (95:5). The product was obtained as a tan crystalline solid, (720 mg, 1.92 mmol).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 36 hours
  3. filtrationfiltered
  4. washthe solid was washed with ethyl acetate-hexane
  5. concentrationThe filtrate was concentrated
  6. customthe residue was chromatographed on silica gel (100 g)
  7. customThe product was obtained as a tan crystalline solid, (720 mg, 1.92 mmol)

Quellen und Nachweise

ORD-Eintrag
ord-ea5e65266bbd4132bb8757ab23bef667
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06518279B2

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