p-Toluenesulfonic acid monohydrate → 4-(2-Chlorophenyl)-6,8-dimethyl-3-quinolinecarbonitrile

HRID 1656441Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1656441
[NH2:1][C:2]1[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=O.CO[C:21](OC)([CH3:24])[C:22]#[N:23].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:4]1[C:3]2[C:2](=[C:16]([CH3:17])[CH:15]=[C:14]([CH3:18])[CH:13]=2)[N:1]=[CH:24][C:21]=1[C:22]#[N:23]

Komponenten

5

Edukt 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 127293742,2-DimethoxypropanenitrileHCID 149185372-Amino-2'-chloro-3,5-dimethylbenzophenone

Produkt 1

HCID 103796024-(2-Chlorophenyl)-6,8-dimethyl-3-quinolinecarbonitrileAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 2-amino-2'-chloro-3,5-dimethylbenzophenone (20.0 g), 2,2-dimethoxypropionitrile (11.5 g), p-toluenesulfonic acid hydrate (1.46 g) and toluene (200 ml) was refluxed for 3 hrs., with removal of water by a Dean-Stark apparatus. The mixture was washed with sodium hydrogen carbonate solution and water, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The resultant precipitate was collected by filtration and washed with hexane to give 4-(2-chlorophenyl)-6,8-dimethyl-3-quinolinecarbonitrile (20.7 g, 92.0%), which was recrystallized from ethanol to give pale yellow plates. m.p. 153°-154° C.

Aufarbeitung

  1. temperaturewas refluxed for 3 hrs
  2. custom, with removal of water by a Dean-Stark apparatus
  3. washThe mixture was washed with sodium hydrogen carbonate solution and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled
  6. customto remove the solvent
  7. filtrationThe resultant precipitate was collected by filtration
  8. washwashed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-819f1a47112b4abb83b00e3065ce4c72
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05254565

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