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

HRID 748317Notes

Reaction equation

HRID 748317 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].ClC1C=CC=C(C(OO)=[O:23])C=1>C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH+:7]([O-:23])[C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 112063492-(Boc-amino)pyridine

Product 1

HCID 86596466tert-Butyl 2-pyridylcarbamate N-oxideYield 95.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 2-pyridylcarbamate (7.4 g, 38 mmol) and 3-chloroperbenzoic acid (77%, 11.2 g, 50 mmol) were dissolved in ethyl acetate (100 ml), and the mixture was stirred at room temperature for 20 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with methanol-ethyl acetate (1:20, v/v) were collected and concentrated to give the titled compound (7.6 g, 95%).

Workup

  1. customThe solvent was evaporated
  2. washThe fractions eluted with methanol-ethyl acetate (1:20
  3. customv/v) were collected
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-894e8f642a7f4c4b88c105b4c7bc4f9c
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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