Methanesulfonyl chloride → N-(2-Methylquinolin-6-yl)methanesulfonamide

HRID 467103

Reaction equation

HRID 467103 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([CH3:17])[CH:11]=[CH:10]2>N1C=CC=CC=1>[CH3:1][S:2]([NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([CH3:17])[CH:11]=[CH:10]2)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 1031482-Methylquinolin-6-amine

Product 1

HCID 19813426N-(2-Methylquinolin-6-yl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (6.2 ml) was added dropwise to a stirred solution of 6-amino-2-methylquinoline (12.5 g) in pyridine (100 ml) cooled to 5°. Stirring was continued for 17 hours at room temperature. The pyridine was then removed by evaporation in vacuo, the residue diluted with aqueous sodium bicarbonate, and extracted three times with methylene chloride. The combined organic extracts were combined, dried (MgSO4) and evaporated in vacuo to give the title compound, yield 13.0 g, m.p. 151°-153°.

Workup

  1. temperaturecooled to 5°
  2. customThe pyridine was then removed by evaporation in vacuo
  3. additionthe residue diluted with aqueous sodium bicarbonate
  4. extractionextracted three times with methylene chloride
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-907df6cfe4be470890ec45e3296d630e
Source dataset
uspto-grants-1992_10
Patent number
US05158964

Linked notes

Loading…