m-Chloroperbenzoic acid → tert-Butyl 2-pyridinecarboxylate N-oxide

HRID 748153Notes

Reaction equation

HRID 748153 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].ClC1C=CC=C(C(OO)=[O:22])C=1>C(OCC)(=O)C>[N+:1]1([O-:22])[C:2]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11126842Tert-butyl Pyridine-2-carboxylate

Product 1

HCID 68456092tert-Butyl 2-pyridinecarboxylate N-oxideYield 81.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 2-pyridinecarboxylate (14.0 g, 78 mmol) was dissolved in ethyl acetate (200 ml), and 3-chloroperbenzoic acid (ca. 77%, 26.2 g, 117 mmol) was added thereto. The reaction mixture was stirred at room temperature for 40 hrs. The solvent was evaporated under reduced pressure. The residue was subjected to a silica gel column chromatography and eluted with ethyl acetate-acetone (1:1, v/v) to give the titled compound (12.4 g, 81%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washeluted with ethyl acetate-acetone (1:1

Sources & evidence

ORD record
ord-b2518ab502a74d668f21a4ad05ca355d
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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