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

HRID 2260551Notes

Reaction equation

HRID 2260551 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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. Then, 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.

Workup

  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

Sources & evidence

ORD record
ord-e2a7b67cba2d4195af7d7e89da5aa527
Source dataset
uspto-grants-1995_12
Patent number
US05478832

Reaction notes

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