2-Bromo-6-methyl-4-nitro-1-oxo-1lambda~5~-pyridine → HCID 86649695, compound

HRID 37859Notes

Reaction equation

HRID 37859 reaction equation
[CH3:1][O-:2].[Na+].[Br:4][C:5]1[CH:10]=[C:9]([N+]([O-])=O)[CH:8]=[C:7]([CH3:14])[N+:6]=1[O-:15]>CO>[Br:4][C:5]1[CH:10]=[C:9]([O:2][CH3:1])[CH:8]=[C:7]([CH3:14])[N+:6]=1[O-:15]

Participants

4

Reactant 2

HCID 27518162-Bromo-6-methyl-4-nitro-1-oxo-1lambda~5~-pyridineHCID 10942334Sodium Methoxide

Product 1

HCID 86649695HCID 86649695, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (94 mg, 1.74 mmol) was added to a solution of 2-bromo-6-methyl-4-nitro-pyridine 1-oxide (408 mg, 1.74 mmol) in dry methanol (20 mL) at 0° C., then warmed to ambient temperature and maintained overnight. The volatiles were evaporated in vacuo and the residue extracted with chloroform (5×40 mL). The combined organic layers were washed with water, dried over anhydrous sodium sulfate and concentrated to afford a residue which was purified by column chromatography over silica gel (60-120 mesh) using 3% methanol in chloroform as eluent to afford 2-bromo-4-methoxy-6-methyl-pyridine 1-oxide (0.32 g, 84%) as a white solid.

Workup

  1. temperaturemaintained overnight
  2. customThe volatiles were evaporated in vacuo
  3. extractionthe residue extracted with chloroform (5×40 mL)
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto afford a residue which
  8. customwas purified by column chromatography over silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-31f2c44b86c145f581675c3dc888c4b3
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

Loading…