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

HRID 1656441ノート

反応式

HRID 1656441 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-819f1a47112b4abb83b00e3065ce4c72
出典データセット
uspto-grants-1993_10
特許番号
US05254565

反応ノート

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