Trimethyl orthovalerate → 2-butyl-1-(3-methylsulfanylpropyl)-7-phenyl-1H-imidazo[4,5-c]quinoline

HRID 1818115

Reaktionsgleichung

Reaktionsgleichung von HRID 1818115
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[NH2:23].[C:24](OC)(OC)(OC)[CH2:25][CH2:26][CH2:27][CH3:28].Cl.N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:25]([C:24]1[N:6]([CH2:5][CH2:4][CH2:3][S:2][CH3:1])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:23]=1)[CH2:26][CH2:27][CH3:28]

Komponenten

5

Edukt 3

HCID 83755Trimethyl orthovalerateHCID 10176127Pyridinium chlorideHCID 86593757N4-(3-methylsulfanylpropyl)-7-phenylquinoline-3,4-diamine

Produkt 1

HCID 219844302-butyl-1-(3-methylsulfanylpropyl)-7-phenyl-1H-imidazo[4,5-c]quinolineAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

N4-(3-Methylsulfanylpropyl)-7-phenylquinoline-3,4-diamine (2.75 g, 8.49 mmol), trimethyl orthovalerate (1.7 g, 10 mmol), and pyridine hydrochloride (0.3 g) were dissolved in toluene (28 mL) and heated to reflux for 1.5 h, collecting the volatiles in a Dean-Stark trap. Upon cooling to room temperature, the solvent was removed under vacuum. The resulting solid was slurried in hexanes (100 mL) for 1 h and then collected by filtration to afford 3.0 g of 2-butyl-1-(3-methylsulfanylpropyl)-7-phenyl-1H-imidazo[4,5-c]quinoline.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 1.5 h
  3. customcollecting the volatiles in a Dean-Stark trap
  4. customthe solvent was removed under vacuum
  5. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-c0cd15c2230a47309c6c01de86410bfe
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598382B2

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