m-Chloroperbenzoic acid → 1-methyl-3-(methylsulfonyl)cinnolin-4(1H)-one

HRID 1578497Notes

Reaction equation

HRID 1578497 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=[O:23])[C:15]([S:24]([CH3:26])=[O:25])=[N:14]1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH3:12][N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=[O:23])[C:15]([S:24]([CH3:26])(=[O:9])=[O:25])=[N:14]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 218236821-Methyl-3-(methylsulfinyl)-4(1H)-cinnolinone

Product 1

HCID 124214871-methyl-3-(methylsulfonyl)cinnolin-4(1H)-oneYield 104.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A quantity of 6.16 g (0.027 mole) of 85% m-chloroperbenzoic acid was added to a solution of 6.6 g (0.03 mole) of 1-methyl-3-(methylsulfinyl)-4(1H)-cinnolinone in 100 ml of chloroform. The temperature rose to 45° C. After 5 minutes the solution was brought to reflux for 5 minutes, cooled, mixed with 200 ml of 5% sodium bicarbonate and stirred for 10 minutes. Additional chloroform (300 ml) was added to dissolve the separated product. The organic layer was separated, dried over anhydrous potassium carbonate and concentrated to give 6.7 g (94.4%) of white product melting at 202°-204°. Recrystallization from chloroform-methanol gave pure product melting at 204°-206° C.

Workup

  1. customrose to 45° C
  2. temperatureto reflux for 5 minutes
  3. temperaturecooled
  4. dissolutionto dissolve the separated product
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous potassium carbonate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a5d0970e8e6941e6bcc813140bc25dd4
Source dataset
uspto-grants-1976_02
Patent number
US03937704

Reaction notes

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