5,6,7,8-Tetrahydroquinoline → 1-(4-chlorophenyl)-8,9-dihydro-7H-pyrrolo[3,2,1-ij]quinolin

HRID 263425

Reaktionsgleichung

Reaktionsgleichung von HRID 263425
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl:11][C:12]1[CH:21]=[CH:20][C:15]([C:16](=O)[CH2:17]Br)=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[Cl:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]2[C:9]3=[C:10]4[C:5]([CH2:6][CH2:7][CH2:8]3)=[CH:4][CH:3]=[CH:2][N:1]4[CH:17]=2)=[CH:14][CH:13]=1

Komponenten

4

Edukt 2

HCID 663355,6,7,8-TetrahydroquinolineHCID 68303p-Chlorophenacyl bromide

Produkt 1

HCID 190380231-(4-chlorophenyl)-8,9-dihydro-7H-pyrrolo[3,2,1-ij]quinolin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

5,6,7,8-Tetrahydroquinoline (35 g) was dissolved in 500 ml of toluene. To this solution was added 4-chlorophenacyl bromide (61.4 g) gradually and refluxed for 1 hour. The reaction mixture was cooled to room temperature, and depositing crystals were collected by filtration (86 g). These solids were dissolved in 500 ml of N,N-dimethylformamide. To this solution was added, molecular sieves 3A (50 g) and triethylamine (44 ml), then the reaction mixture was heated at 100° C. for 1 hour. The reaction mixture became dark brown. The dark brown solution that obtained after removing insoluble matter by filtration was concentrated under reduced pressure. The resultant brown solids were recrystallized from ethanol (300 ml), and the title compound was obtained as colorless leaflets (50 g).

Aufarbeitung

  1. temperaturerefluxed for 1 hour
  2. filtrationdepositing crystals were collected by filtration (86 g)
  3. dissolutionThese solids were dissolved in 500 ml of N,N-dimethylformamide
  4. additionTo this solution was added
  5. temperaturemolecular sieves 3A (50 g) and triethylamine (44 ml), then the reaction mixture was heated at 100° C. for 1 hour
  6. customThe dark brown solution that obtained
  7. customafter removing insoluble matter
  8. filtrationby filtration
  9. concentrationwas concentrated under reduced pressure
  10. customThe resultant brown solids were recrystallized from ethanol (300 ml)

Quellen und Nachweise

ORD-Eintrag
ord-636dda78ccdc4525847198ac82cbfc45
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05643920

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