Sodium Carbonate → 5-Phenyl-2-picoline N-oxide

HRID 363196

Reaction equation

HRID 363196 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:22])C=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:1]1([C:7]2[CH:8]=[N+:9]([O-:22])[C:10]([CH3:13])=[CH:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 767442-Methyl-5-phenylpyridine

Product 1

HCID 149805285-Phenyl-2-picoline N-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-phenyl-6-methyl pyridine (2.36 g, 13.95 mmol), in CH2Cl2 (40 mL) at 0° C. was treated with MCPBA (3.58 g, 13.95 mmol) for 1 hour. Saturated aq. Na2CO3 (50 mL) was added and the reaction was extracted with CH2Cl2 (20 mL). The organic extracts were dried (MgSO4), and the solvent evaporated in vacuo to afford the title compound.

Workup

  1. extractionthe reaction was extracted with CH2Cl2 (20 mL)
  2. dry with materialThe organic extracts were dried (MgSO4)
  3. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-05a8840426d74b2e8630c01407e52f00
Source dataset
uspto-grants-1999_02
Patent number
US05872136

Linked notes

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