m-Chloroperbenzoic acid → 2-(Chloromethyl)-3-(methoxycarbonyl)pyridine 1-oxide

HRID 1799544Notes

Reaction equation

HRID 1799544 reaction equation
[Cl:1][CH2:2][C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=[CH:5][N:4]=1.C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)Cl>[Cl:1][CH2:2][C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=[CH:5][N+:4]=1[O-:21]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19081344Methyl 2-(chloromethyl)pyridine-3-carboxylate

Product 1

HCID 582166522-(Chloromethyl)-3-(methoxycarbonyl)pyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(chloromethyl)pyridine-3-carboxylate (4.45 g, 23.98 mmol) was taken up in DCM (50 mL) and mCPBA (5.91 g, 26.4 mmol) was added. The resulting solution was stirred at room temperature overnight. The reaction mixture was then purified directly by silica gel chromatography (0-20% MeOH/EtOAe) to give methyl 2-(chloromethyl)pyridine-3-carboxylate 1-oxide as a white solid.

Workup

  1. customThe reaction mixture was then purified directly by silica gel chromatography (0-20% MeOH/EtOAe)

Sources & evidence

ORD record
ord-f9239f87dfc24a56b8a9ae73508168ab
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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