2-Phenylpyridine → 2-Phenylpyridine 1-Oxide

HRID 418051Notes

Reaction equation

HRID 418051 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:12]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N+:19]=2[O-:9])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 138872-PhenylpyridineHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 3024892-Phenylpyridine 1-OxideYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-chloroperbenzoic acid (19 g) was added portionwise to an ice-cold solution of 2-phenylpyridine (10 g) in DCM (30 ml). The mixture was allowed to warm to RT and was stirred at RT for 4 h. 100 ml of a NaHCO3 solution were added to the reaction mixture and the phases were separated. The aq. phase was further extracted with DCM and the combined org. phases were washed with an aq. NaHSO3 (40%) solution and evaporated off. Recrystallisation (EA) afforded 8.77 g of the desired compound.

Workup

  1. customthe phases were separated
  2. extractionThe aq. phase was further extracted with DCM
  3. washphases were washed with an aq. NaHSO3 (40%) solution
  4. customevaporated off
  5. customRecrystallisation (EA)

Sources & evidence

ORD record
ord-a44663e670ec4b0d82d1353224ea7e0e
Source dataset
uspto-grants-2012_01
Patent number
US08093250B2

Reaction notes

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