Phthalic Anhydride → 3-Chloro-4-methoxy-2,5-dimethylpyridine 1-oxide

HRID 81694Notes

Reaction equation

HRID 81694 reaction equation
[Cl:1][C:2]1[C:3]([CH3:11])=[N:4][CH:5]=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9].C(N)(N)=[O:13].OO.C1(=O)OC(=O)C2=CC=CC=C12.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([CH3:11])=[N+:4]([O-:13])[CH:5]=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9]

Participants

7

Reactant 4

HCID 6811Phthalic AnhydrideHCID 24477Sodium ThiosulfateHCID 31294Carbamide PeroxideHCID 582012143-Chloro-4-methoxy-2,5-dimethylpyridine

Product 1

HCID 143691543-Chloro-4-methoxy-2,5-dimethylpyridine 1-oxideYield 91.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

The above 3-chloro-4-methoxy-2,5-dimethylpyridine (181 mg) was dissolved in 5 ml of dichloromethane, and urea peroxide (169 mg) and phthalic anhydride (219 mg) were then added to the solution. The resulting mixture was stirred at room temperature for 2.5 hours. Thereafter, a saturated aqueous sodium thiosulfate solution was added to the reaction solution under cooling on ice, and the resulting mixture was then diluted with chloroform. The water layer was extracted with chloroform two times. The organic layer was dried over anhydrous sodium sulfate, and the solvent was then distilled away, so as to obtain the title compound (181 mg) as a solid.

Workup

  1. temperatureunder cooling on ice
  2. extractionThe water layer was extracted with chloroform two times
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was then distilled away

Sources & evidence

ORD record
ord-dbb251982fd84cea88e23d9109cbe504
Source dataset
uspto-grants-2014_09
Patent number
US08846703B2

Reaction notes

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