4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 2-acetyl-quinolin-3-yl ester

HRID 502623Notes

Reaction equation

HRID 502623 reaction equation
[OH:1][C:2]1[C:3]([C:12](=[O:14])[CH3:13])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C(N(CC)CC)C.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>ClCCl>[C:12]([C:3]1[C:2]([O:1][S:28]([C:25]2[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=2)(=[O:30])=[O:29])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 196921842-Acetyl-3-quinolinol

Product 1

HCID 86098625Toluene-4-sulfonic acid 2-acetyl-quinolin-3-yl esterYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (5° C.) solution of 1-(3-Hydroxy-quinolin-2-yl)-ethanone (1.96 g, 10.5 mmol) in 100 mL dichloromethane was added triethylamine (1.59 g, 2.19 mL. 15.75 mmol). After 10 minutes p-toluenesulfonyl chloride (2.191 g, 11.5 mmol) was added and the mixture was stirred at room temperature for 18 hours. The mixture was washed with 1N HCl, water, and brine, dried (MgSO4) and concentrated under reduced pressure to afford 3.58 g of toluene-4-sulfonic acid 2-acetyl-quinolin-3-yl ester.

Workup

  1. washThe mixture was washed with 1N HCl, water, and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84f219706c0a42ba9a4e5215fd1fc26c
Source dataset
uspto-grants-2010_08
Patent number
US07776872B2

Reaction notes

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