Sodium Bicarbonate → HCID 70682014, compound

HRID 2071161Notes

Reaction equation

HRID 2071161 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].C([O-])(O)=[O:14].[Na+]>CC(O)=O.OO>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[C:10]([CH3:12])[N+:11]=1[O-:14]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 2759833Methyl 2-Chloro-6-methylisonicotinate

Product 1

HCID 70682014HCID 70682014, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 784Hydrogen PeroxideSolvent2×

Procedure

A solution of 6.05 g (32.6 mmol) of methyl 2-chloro-6-methylisonicotinate (Aldrich) in 30 mL of AcOH and 30 mL of H2O2 (30 wt. % in H2O) was stirred at 135° C. for 45 min. and 9 mL of H2O2 (30 wt. % in water) was added. Heating was continued for 3 h, and saturated NaHCO3 solution was added to pH=8. The aqueous layer was extracted with EtOAc (4×), and the combined extracts were washed with 100 mL of brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (80% EtOAc/hexanes) provided 4.1 g of the 2-chloro-4-(methoxycarbonyl)-6-methylpyridine 1-oxide as an off-white solid in 63% yield.

Workup

  1. temperatureHeating
  2. extractionThe aqueous layer was extracted with EtOAc (4×)
  3. washthe combined extracts were washed with 100 mL of brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash silica gel chromatography (80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-783dfe31cee14e18852376e56d841faf
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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