Methyl 6-methylnicotinate 1-oxide → Methyl 6-(acetoxymethyl)nicotinate

HRID 348998Notes

Reaction equation

HRID 348998 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[O-]>C(OC(=O)C)(=O)C>[C:6]([O:8][CH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1)(=[O:7])[CH3:5]

Participants

3

Reactant 1

HCID 15883477Methyl 6-methylnicotinate 1-oxide

Product 1

HCID 10353032Methyl 6-(acetoxymethyl)nicotinateYield 121.2%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

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. concentrationconcentrated under reduced pressure
  2. customPurification by flash column chromatography (silica gel, 1:2 to 3:5 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-aeb2713e5cf54385b03239a355fe75c8
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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