Sodium Sulfite → 4-(4-Methoxycarbonylphenyl)pyridine N-oxide

HRID 459543Notes

Reaction equation

HRID 459543 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:25])C=1.S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[CH3:14][O:13][C:11]([C:10]1[CH:15]=[CH:16][C:7]([C:4]2[CH:5]=[CH:6][N+:1]([O-:25])=[CH:2][CH:3]=2)=[CH:8][CH:9]=1)=[O:12]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 5152686Methyl 4-(4-pyridinyl)benzoate

Product 1

HCID 186176494-(4-Methoxycarbonylphenyl)pyridine N-oxideYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 4-(4-pyridyl)benzoate (1.49 g) was dissolved in dichloromethane (30 ml), 70% m-chloroperbenzoic acid (3.46 g) was added, and the mixture was stirred at room temperature for 1 hour. An aqueous solution of sodium sulfite was added to conduct liquid separation. The resultant organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and then dried over anhydrous sodium sulfate. The solvent was distilled off to obtain the title compound (1.33 g) as white powder.

Workup

  1. customliquid separation
  2. washThe resultant organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-68df5064f26c4397add692bd11fca849
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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