Dimethyl Sulfoxide → 4-[(3-Bromophenyl)amino]-6,7-diethoxyquinoline-3-carbonitrile

HRID 612012Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 612012
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15](O)=[C:16]([OH:19])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:21]#[N:22])[CH:5]=[CH:6][CH:7]=1.[CH2:23](I)[CH3:24].[C:26](=[O:29])([O-])[O-].[K+].[K+].[CH3:32]S(C)=O>>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:29][CH2:26][CH3:32])=[C:16]([O:19][CH2:23][CH3:24])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:21]#[N:22])[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 4

HCID 679Dimethyl SulfoxideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 1354028484-(3-Bromophenylamino)-6,7-dihydroxy-3-quinolinecarbonitrile

Produkt 1

HCID 53288384-[(3-Bromophenyl)amino]-6,7-diethoxyquinoline-3-carbonitrile

Versuchsvorschrift

A mixture of 0.36 g of 4-[(3-bromophenyl)amino]-6,7-dihydroxy-3-quinolinecarbonitrile, 0.32 ml of ethyl iodide and 0.55 g of potassium carbonate in 4 ml of dimethylsulfoxide was stirred for 3 hours in an oil bath with heating. Most of the solvent was removed at reduced pressure. The mixture was mixed with ethyl acetate and water. The organic layer was washed with water and dried over magnesium sulfate. Solvent was removed to give 0.23 g of 4-[(3-bromophenyl)amino]-6,7-diethoxy-3-quinolinecarbonitrile which after recrystallization from ethyl acetate gave mp=173-175° C.

Aufarbeitung

  1. temperaturewith heating
  2. customMost of the solvent was removed at reduced pressure
  3. additionThe mixture was mixed with ethyl acetate and water
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customSolvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-f00f6776575e4bb487d25cb3ac4a58e8
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06002008

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