Sodium Thiosulfate → Methyl 6-phenylpyridine-2-carboxylate 1-oxide

HRID 2095779Notes

Reaction equation

HRID 2095779 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:25])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[C:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[N+:12]=2[O-:25])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 11127604Methyl 6-phenylpyridine-2-carboxylate

Product 1

HCID 66968602Methyl 6-phenylpyridine-2-carboxylate 1-oxideYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 6-phenylpyridine-2-carboxylate (509 mg, 6.24 mmol) in dichloromethane (5 mL) was added m-chloroperbenzoic acid (purity: 69-75%, 2.87 g, 12.5 mmol), and the mixture was stirred at room temperature for 3 days. Saturated sodium thiosulfate aqueous solution was added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/hexane=1/2→1/1) to give the title compound (142 mg, 10%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/hexane=1/2→1/1)

Sources & evidence

ORD record
ord-73b9332c468240609e0f805f3f167ae1
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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