Aniline → 2-ethyl-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline

HRID 37617

Reaktionsgleichung

Reaktionsgleichung von HRID 37617
[CH2:1]([C:3]1[CH2:12][C:11](=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2].NC1C=CC=CC=1.C(CC(OCC)=O)(=O)CC.C(=O)([O-])[O-].[K+].[K+].Br[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[C:51]2[N:55]([C:56]3[CH:61]=[CH:60][C:59]([N+:62]([O-:64])=[O:63])=[CH:58][CH:57]=3)[N:54]=[N:53][N:52]=2)=[CH:41][CH:40]=1>CN1C(=O)CCC1.O>[CH2:1]([C:3]1[CH:12]=[C:11]([O:13][CH2:38][C:39]2[CH:40]=[CH:41][C:42]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=3[C:51]3[N:55]([C:56]4[CH:61]=[CH:60][C:59]([N+:62]([O-:64])=[O:63])=[CH:58][CH:57]=4)[N:54]=[N:53][N:52]=3)=[CH:43][CH:44]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2]

Komponenten

8

Edukt 5

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 78656Ethyl 3-oxovalerateHCID 150208512-ethyl-3H-quinolin-4-oneHCID 199357915-(4'-bromomethylbiphenyl-2-yl)-1-(4-nitrophenyl)-1H-tetrazole

Produkt 1

HCID 199357842-ethyl-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinolineAusbeute 28,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2-ethyl-4-quinolone (1.9 g; 11 mmol), (prepared using a similar procedure to that described in Org. Syn., Coll., Vol. III, p. 374 and p. 593 from aniline and ethyl propionylacetate), and potassium carbonate (2.28 g; 16 mmol) in NMP (75 ml) was heated at 60° C. for 20 minutes with stirring. Compound E (5.2 g; 10 mmol) was added and the reaction mixture 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]quinoline (A) (1.5 g) as a solid, m.p. 204°-206° C.; NMR (CDCl3): 1.42(3H, t), 3.0(2H, q), 5.23(2H, s), 6.67(2H, d), 6.75(1H, s), 6.85(2H, d), 7.25(2H, d), 7.43(1H, d), 7.55(1H, t), 7.70(3H, m) 7.90(3H, d), 8.05(1H, d), 8.20(1H, d).

Aufarbeitung

  1. custom(prepared
  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-0f56728b7c524dc3894f2e8e9c5bc806
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420292

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