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

HRID 1656441Notes

Reaction equation

HRID 1656441 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-819f1a47112b4abb83b00e3065ce4c72
Source dataset
uspto-grants-1993_10
Patent number
US05254565

Reaction notes

Loading…