Nitric Acid → 2-Bromo-6-methyl-4-nitro-1-oxo-1lambda~5~-pyridine

HRID 37858

Reaction equation

HRID 37858 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N+:12]=1[O-:18].C(=O)(O)[O-].[Na+]>>[Br:10][C:11]1[CH:16]=[C:15]([N+:1]([O-:4])=[O:2])[CH:14]=[C:13]([CH3:17])[N+:12]=1[O-:18]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 36520842-Bromo-6-methylpyridine 1-oxide

Product 1

HCID 27518162-Bromo-6-methyl-4-nitro-1-oxo-1lambda~5~-pyridineYield 40%

Conditions

Temperature
70 °C

Procedure

Concentrated nitric acid (4 mL) was added to cold concentrated sulfuric acid (7 mL). 2-Bromo-6-methyl-pyridine 1-oxide (820 mg, 4.36 mmol) was added to this and then heated at 70° C. for 4 h. The mixture was cooled and poured slowly into ice-cold water (100 mL) and basified to pH ˜8 with sodium bicarbonate solution. This was extracted with ethyl acetate (4×50 mL) then the combined organic layers were dried over anhydrous sodium sulfate and concentrated to give a residue which was purified by washing with pentane (50 mL) to afford 2-bromo-6-methyl-4-nitro-pyridine 1-oxide (0.41 g, 40%) as a free flowing yellow solid.

Workup

  1. temperatureThe mixture was cooled
  2. extractionThis was extracted with ethyl acetate (4×50 mL)
  3. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto give a residue which
  6. customwas purified
  7. washby washing with pentane (50 mL)

Sources & evidence

ORD record
ord-9f7ac09e91f147b1838c657ff9dbbc63
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Linked notes

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