m-Chloroperbenzoic acid → Methyl 2-methylnicotinate 1-oxide

HRID 2277612Notes

Reaction equation

HRID 2277612 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[CH3:10].C1C=C(Cl)C=C(C(OO)=[O:20])C=1>C(Cl)Cl>[CH3:1][O:2][C:3]([C:4]1[C:5]([CH3:10])=[N+:6]([O-:20])[CH:7]=[CH:8][CH:9]=1)=[O:11]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 7015327Methyl 2-methylnicotinate

Product 1

HCID 20163965Methyl 2-methylnicotinate 1-oxideYield 57.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl-2-methylnicotinate (95 g, 629 mmol) in DCM (1.5 L) was added m-CPBA (119 g, 692 mmol) at 0° C. After the reaction mixture was stirred at room temperature for 16 hours, it was washed with a mixture of satd. aq. Na2SO3 and NaHCO3 solution. The organic layer was then dried over anhy. Na2SO4, filtered, and concentrated in vacuo to give a crude product (60 g, yield 57%), which was used in the next step reaction without further purification.

Workup

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

Sources & evidence

ORD record
ord-1aaa62396e604fa09a7a813fbe7db835
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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