8-Aminoquinoline → 8-(Methylsulfonylamino)quinoline

HRID 1006387Notes

Reaction equation

HRID 1006387 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH3:12][S:13](Cl)(=[O:15])=[O:14]>N1C=CC=CC=1>[CH3:12][S:13]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 31297Methanesulfonyl chloride

Product 1

HCID 1515068-(Methylsulfonylamino)quinolineYield 92.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The reaction of 5.0 g (0.0347 mole) of 8-aminoquinoline with 3.97 g (0.0347 mole) of methylsulfonyl chloride was carried out in 10 ml of pyridine at room temperature. After 2 hours from the start of the reaction, the reaction mixture was washed with water, extracted with diethyl ether, purified by column chromatography and concentrated to give 10.32 g (0.032 mole, 92%) of 8-(methylsulfonamido)quinoline. Then, 5.0 g (0.016 mole) of the 8-(methylsulfonamido)quinoline, 3.07 g (0.023 mole) of zinc chloride and 6.98 g (0.069 mole) of triethylamine were suspended in 30 ml of ethanol and allowed to react at room temperature. After 3 hours, the separated yellow powder was filtered, washed with ethanol and purified by column chromatography to give 10.48 g (90.0%) of Compound M as yellow crystals. The maximum PL wavelength of this compound in chloroform was 505 nm.

Workup

  1. customAfter 2 hours from the start of the reaction
  2. washthe reaction mixture was washed with water
  3. extractionextracted with diethyl ether
  4. custompurified by column chromatography
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e6f419eaed3e4bbc8e2cf945a1fe2685
Source dataset
uspto-grants-2004_09
Patent number
US06790540B2

Reaction notes

Loading…