Ethyl Nicotinate → MLS002693958

HRID 1471703Notes

Reaction equation

HRID 1471703 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:20])C=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N+:8]([O-:20])[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 69188Ethyl NicotinateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 253138MLS002693958

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold solution of 3-ethoxycarbonylpyridine (25 g, 165.4 mmol, 1 eq) in DCM was slowly added mCPBA (70% wt, 198.5 mmol) and the reaction mixture was stirred at rt overnight. Reaction was cooled and diluted with DCM and then neutralized with slow addition of sat. NaHCO3. Aqueous layer was washed with DCM (3×) and the combined organic layer was dried and evaporated to give a residue, which was purified by column chromatography (EtOAc/MeOH) to give 3-ethoxycarbonylpyridine N-oxide (13.6 g). MS: exact mass calculated for C8H9NO3, 167.06; m/z found, 168 [M+H]+.

Workup

  1. customReaction
  2. temperaturewas cooled
  3. washAqueous layer was washed with DCM (3×)
  4. customthe combined organic layer was dried
  5. customevaporated
  6. customto give a residue, which
  7. customwas purified by column chromatography (EtOAc/MeOH)

Sources & evidence

ORD record
ord-295c12fab5eb4237bdfc604ed8a1d431
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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