Biphenyl → 4-Hydroxyquinoline-6-carbonitrile

HRID 1072873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1072873
C1(C2C=CC=CC=2)C=CC=CC=1.C1(OC2C=CC=CC=2)C=CC=CC=1.[C:26]([C:28]1[CH:33]=[CH:32][C:31]([NH:34][CH:35]=[C:36]2[C:41](=[O:42])OC(C)(C)OC2=O)=[CH:30][CH:29]=1)#[N:27]>CCCCCC>[OH:42][C:41]1[C:30]2[C:31](=[CH:32][CH:33]=[C:28]([C:26]#[N:27])[CH:29]=2)[N:34]=[CH:35][CH:36]=1

Komponenten

5

Edukt 3

HCID 7095BiphenylHCID 7583Diphenyl EtherHCID 116947054-(((2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzonitrile

Produkt 1

HCID 116583514-Hydroxyquinoline-6-carbonitrileAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
250 °C

Versuchsvorschrift

A mixture of biphenyl (10 ml) and diphenyl ether (30 ml) was heated at 250° C. and 5-(4-cyanophenylamino)methylidene-2,2-dimethyl-1,3-dioxane-4,6-dione (3.28 g) was added thereto. The mixture was stirred for 1 hr. The reaction mixture was cooled to 80° C. while stirring and hexane (100 ml) was added. The mixture was stirred in an ice bath for 0.5 hr. The resulting solid was collected by filtration and washed with hexane to give the object compound (1.86 g) as a yellow-brown powder.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to 80° C.
  2. stirringwhile stirring
  3. stirringThe mixture was stirred in an ice bath for 0.5 hr
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-6160073082b7493292cbb71fe5dd7b77
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911469B2

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