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

HRID 631835Notes

Reaction equation

HRID 631835 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[C:4]([CH3:11])[N+:3]=1[O-:12].[CH3:13][O-:14].[Na+]>CO.O>[Br:1][C:2]1[CH:7]=[C:6]([O:14][CH3:13])[CH:5]=[C:4]([CH3:11])[N+:3]=1[O-:12]

Participants

5

Reactant 2

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

Product 1

HCID 86649695HCID 86649695, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-Bromo-6-methyl-4-nitro-pyridine 1-oxide (4 g, 17 mmol) was dissolved in methanol (anhydrous, 100 ml), and sodium methoxide (1.8 g, 33 mmol) was added. The mixture was stirred at room temperature for 90 minutes, diluted with water (90 ml) and concentrated under reduced pressure to half of its volume. The mixture was extracted with DCM (5×), the combined organic phases were dried (sodium sulfate) and concentrated to dryness under reduced pressure to yield 3.3 g of yellow crystals, 15 mmol, 88%) MS(APCI) m/z=217.9 [M+1]+.

Workup

  1. concentrationconcentrated under reduced pressure to half of its volume
  2. extractionThe mixture was extracted with DCM (5×)
  3. dry with materialthe combined organic phases were dried (sodium sulfate)
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4daef5c52a984db0bedc5345cf2442e0
Source dataset
uspto-grants-2016_04
Patent number
US09321724B2

Reaction notes

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