Water → 2-ethyl-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-5,6,7,8-tetrahydroquinoline

HRID 654377

Reaktionsgleichung

Reaktionsgleichung von HRID 654377
[CH2:1]([C:3]1[NH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11](=[O:13])[CH:12]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].BrC[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]2[N:39]([C:40]3[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=3)[N:38]=[N:37][N:36]=2)=[CH:25][CH:24]=1.O>CN1C(=O)CCC1>[CH2:1]([C:3]1[CH:12]=[C:11]([O:13][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]3[N:39]([C:40]4[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=4)[N:38]=[N:37][N:36]=3)=[CH:27][CH:28]=2)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:4]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 149504752-Ethyl-5,6,7,8-tetrahydroquinolin-4(1H)-oneHCID 53784464HCID 53784464, Verbindung

Produkt 1

HCID 111141832-ethyl-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-5,6,7,8-tetrahydroquinolineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 2-ethyl-5,6,7,8-tetrahydro-4(1H)-quinolone (1.95 g), and potassium carbonate (2.28 g) in NMP (75 ml) was heated at 60° C. for 20 minutes with stirring. Compound E (5.2 g) was added and the reaction mixture was heated at 80° C. for 90 minutes. The mixture was allowed to cool to ambient temperature and water (150 ml) was added. The resultant precipitate was collected by filtration, dried at 60° C., then recrystallised from toluene to give 2-ethyl-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-5,6,7,8-tetrahydroquinoline, as a solid in 60% yield; m.p. 205°-207° C.; NMR (CDCl3):1.30(3H,t), 1.90(4H,m), 2.60-3.00(6H,m), 5.04(2H,m), 6.52(2H,d), 6.60(1H,s), 6.80(2H,d), 7.11(2H,d), 7.40(1H,d), 7.67(2 H,d), 7.92(3H,m).

Aufarbeitung

  1. temperaturethe reaction mixture was heated at 80° C. for 90 minutes
  2. temperatureto cool to ambient temperature
  3. filtrationThe resultant precipitate was collected by filtration
  4. customdried at 60° C.
  5. customrecrystallised from toluene

Quellen und Nachweise

ORD-Eintrag
ord-9506ba8bf91942a6a516711770547747
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05130318

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