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

HRID 2277614Notes

Reaction equation

HRID 2277614 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[CH2:10][Cl:11].C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)Cl>[Cl:11][CH2:10][C:5]1[C:4]([C:3]([O:2][CH3:1])=[O:12])=[CH:9][CH:8]=[CH:7][N+:6]=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-oxideYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl-2-(chloromethyl)nicotinate (20 g, 108 mmol) in DCM (300 mL) was added m-CPBA (20.5 g, 119 mmol) at 0° C. After it was stirred at room temperature for 16 hours, the reaction mixture was washed with a mixture of satd. aq. Na2SO3 and NaHCO3 solution. The organic layer was dried over anhy. Na2SO4, filtered, and concentrated in vacuo to give the crude title product (20 g, yield 92%), which was used in the next step reaction without further purification.

Workup

  1. washthe reaction mixture was washed with a mixture of satd
  2. customThe organic layer was dried over anhy
  3. filtrationNa2SO4, filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-da39907af2fc4546bdc2558c6b94d518
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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