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

HRID 1656441노트

반응식

HRID 1656441 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-819f1a47112b4abb83b00e3065ce4c72
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05254565

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