m-Chloroperbenzoic acid → 6-Methanesulphonamido-2-methylquinoline-1-oxide

HRID 345043Notes

Reaction equation

HRID 345043 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][S:13]([NH:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[C:22]([CH3:27])[CH:21]=[CH:20]2)(=[O:15])=[O:14]>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH3:12][S:13]([NH:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N+:23]([O-:9])=[C:22]([CH3:27])[CH:21]=[CH:20]2)(=[O:14])=[O:15]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19813426N-(2-Methylquinolin-6-yl)methanesulfonamide

Product 1

HCID 198134366-Methanesulphonamido-2-methylquinoline-1-oxide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

m-Chloroperbenzoic acid ("MCPBA") (5.2 g) was added portionwise to a solution of 6-methanesulphonamido-2-methylquinoline (6 g) in methylene chloride and stirring was continued for 17 hours. The reaction mixture was then diluted with aqueous sodium bicarbonate and the organic layer was separated. The aqueous layer was extracted with methylene chloride. The combined organic layers were washed with aqueous sodium bicarbonate, dried (MgSO4) and evaporated in vacuo to give a solid which was recrystallised from ethanol to give the title compound, yield 1.6 g, m.p. 241°-243°.

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted with methylene chloride
  3. washThe combined organic layers were washed with aqueous sodium bicarbonate
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customto give a solid which
  7. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-c02addb57b82406b9d8249336e29e103
Source dataset
uspto-grants-1991_10
Patent number
US05055473

Reaction notes

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