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4-Toluenesulfonyl chloride → 2-(6-Methylquinolin-2-yl)benzonitrile

HRID 1377967
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1377967
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([NH2:16])=O)[CH:6]=[CH:5]2.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]#[N:16])[CH:6]=[CH:5]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 229156312-(6-Methylquinolin-2-yl)benzamide

Produkt 1

HCID 218042392-(6-Methylquinolin-2-yl)benzonitrileAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

15 ml of pyridne were added to 2.05 g (7.82 mmol) of 2-(6-methylquinolin-2-yl)benzamide obtained in Reference Example 7 and the mixture was stirred. Were, 1.49 g (7.82 mmol) of p-toluenesulfonyl chloride were added thereto and stirred at room temperature for 2 hours. After further stirring the mixture at 40° C. for 2 hours, the reaction mixture was poured into 30 ml of water and extracted with 50 ml of methylene chloride. The resulting extract was dried over magnesium sulfate followed by filtration. The filtrate was concentrated and the concentrate was subjected to silica gel chromatography using a mixed solvent of hexane and ethyl acetate (7/1) to obtain 0.86 g of 2-(6-methylquinolin-2-yl)benzonitrile.

Aufarbeitung

  1. customobtained in Reference Example 7
  2. stirringstirred at room temperature for 2 hours
  3. stirringAfter further stirring the mixture at 40° C. for 2 hours
  4. extractionextracted with 50 ml of methylene chloride
  5. extractionThe resulting extract
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfollowed by filtration
  8. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-2beebf658ce547bfb9a06a23e8bca160
Quelldatensatz
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05665881

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