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

HRID 385951Notes

Reaction equation

HRID 385951 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 allowed to react at room temperature overnight and then purified directly by silica gel chromatography (0-20% MeOH-EtOAc) to afford the title compound as a white solid.

Workup

  1. customto react at room temperature overnight
  2. custompurified directly by silica gel chromatography (0-20% MeOH-EtOAc)

Sources & evidence

ORD record
ord-29ea455b19d04b06ba3df77bb0ea3256
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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