Hydrogen Peroxide → Methyl 6-methylnicotinate 1-oxide

HRID 905647Notes

Reaction equation

HRID 905647 reaction equation
[OH:1]O.O.[CH3:4][O:5][C:6]([C:8]1[CH:9]=[N:10][C:11]([CH3:14])=[CH:12][CH:13]=1)=[O:7]>O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+].[O-2].[Mn+2].CO>[CH3:4][O:5][C:6]([C:8]1[CH:9]=[N+:10]([O-:1])[C:11]([CH3:14])=[CH:12][CH:13]=1)=[O:7]

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 231548Methyl 6-methylnicotinate

Product 1

HCID 15883477Methyl 6-methylnicotinate 1-oxideYield 98%

Reagents, catalysts & solvents 3

HCID 150191Sodium Tungstate DihydrateCatalystHCID 160959Manganese oxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

30% Hydrogen peroxide in water (5.7 mL, 50 mmol) and sodium tungstate dihydrate (270 mg, 0.80 mmol) were added to 6-methylpyridine-3-carboxylic acid methyl ester (3.0 g, 20 mmol). The reaction mixture was stirred at 60° C. for 70 minutes and at 80° C. for 4.5 hours. Under ice cooling, methanol (10 mL) and manganese oxide (0.51 g, 6.0 mmol) were added thereto, and then the reaction mixture was stirred at room temperature for 16 hours. After the insoluble was filtered off with celite, the filtrate was concentrated to give 3.2 g of the title reference compound as a pale brown solid. (Yield 98%)

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 16 hours
  2. filtrationAfter the insoluble was filtered off with celite
  3. concentrationthe filtrate was concentrated
  4. customto give 3.2 g of the title reference compound as a pale brown solid

Sources & evidence

ORD record
ord-ee0465031ae84988a2d557362adba341
Source dataset
uspto-grants-2011_09
Patent number
US08012972B2

Reaction notes

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