m-Chloroperbenzoic acid → Methyl 6-methylnicotinate 1-oxide

HRID 348997Notes

Reaction equation

HRID 348997 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:20])C=1>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N+:3]=1[O-:20]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 231548Methyl 6-methylnicotinate

Product 1

HCID 15883477Methyl 6-methylnicotinate 1-oxideYield 92.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 6-methylnicotinate (6.05 g) in methylene chloride (100 mL) was added m-chloroperbenzoic acid (77%, 13.5 g). The reaction mixture was stirred at room temperature for 2 h and then diluted with chloroform (100 mL). The mixture was washed successively with aqueous sodium sulfite, saturated sodium bicarbonate, and brine. The organic later was then dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide 6.21 g of methyl 6-methylnicotinate 1-oxide. A solution of methyl 6-methylnicotinate 1-oxide (4.35 g) in acetic anhydride (50 mL) was heated at 120° C. for 2 h and then concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 1:2 to 3:5 ethyl acetate/hexanes) provided 3.3 g of the title compound: 1H NMR (300 MHz, CDCl3) δ 9.18, 8.31, 7.44, 5.29, 3.96, 2.19.

Workup

  1. washThe mixture was washed successively with aqueous sodium sulfite, saturated sodium bicarbonate, and brine
  2. dry with materialThe organic later was then dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7c6b63dab04f44678562fa5b43f1754f
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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