m-Chloroperbenzoic acid → 2-(Methoxycarbonyl)-3-methylpyridine 1-oxide

HRID 2201578Notes

Reaction equation

HRID 2201578 reaction equation
[CH3:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:20])C=1>C(Cl)Cl>[CH3:11][O:10][C:8]([C:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N+:4]=1[O-:20])=[O:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12264487Methyl 3-methylpyridine-2-carboxylate

Product 1

HCID 727140222-(Methoxycarbonyl)-3-methylpyridine 1-oxideYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 3-methylpicolinate (2 g, 14.8 mmol) and m-CPBA (3 g, 17.8 mmol) in DCM (35 mL) was stirred at RT overnight. Then the mixture was washed with NaHSO3 (a.q.) and concentrated in vacuum. The residue was purified by column chromatography (DCM:MeOH=200:1) to give the product of 2-(methoxycarbonyl)-3-methylpyridine 1-oxide (1.89 g, yield: 79%). 1H-NMR (CDCl3, 400 MHz) δ 8.05 (d, J=6.0 Hz, 1H), 7.18 (t, J=8.4 Hz, 1H), 7.10 (d, J=8.0 Hz, 1H), 3.95 (s, 3H), 2.23 (s, 3H). MS (M+H)+: 168.

Workup

  1. washThen the mixture was washed with NaHSO3 (a.q.)
  2. concentrationconcentrated in vacuum
  3. customThe residue was purified by column chromatography (DCM:MeOH=200:1)

Sources & evidence

ORD record
ord-b40c89c2bfba4f2088bb4080541338d9
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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