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

HRID 631834

Reaction equation

HRID 631834 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N+:7]=1[O-:13]>S(=O)(=O)(O)O>[Br:5][C:6]1[CH:11]=[C:10]([N+:1]([O-:4])=[O:2])[CH:9]=[C:8]([CH3:12])[N+:7]=1[O-:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 36520842-Bromo-6-methylpyridine 1-oxide

Product 1

HCID 27518162-Bromo-6-methyl-4-nitro-1-oxo-1lambda~5~-pyridineYield 57%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
70 °C

Procedure

To cooled nitric acid (concentrated, 168 ml) was added sulfuric acid (concentrated, 300 ml) under cooling followed by 2-bromo-6-methyl-pyridine 1-oxide (35 g, 0.186 mol). The mixture was stirred at 70° C. for 4 hours, cooled to room temperature and poored slowly on crushed ice. A stream of nitrogen was bubbled through the mixture overnight. The mixture was basified to pH 8 under cooling with NaOH (10N, ca. 1 L), diluted with water (3 L) and extracted with DCM (5×). The combined organic phases were dried (sodium sulfate) and evaporated to dryness to yield 27.6 g of a yellow crystaline solid (0.118 mol, 57%).

Workup

  1. temperatureunder cooling
  2. temperaturecooled to room temperature
  3. custompoored slowly on crushed ice
  4. customA stream of nitrogen was bubbled through the mixture overnight
  5. temperatureunder cooling with NaOH (10N, ca. 1 L)
  6. additiondiluted with water (3 L)
  7. extractionextracted with DCM (5×)
  8. dry with materialThe combined organic phases were dried (sodium sulfate)
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-970edf86b814412faf18b6f7474e2814
Source dataset
uspto-grants-2016_04
Patent number
US09321724B2

Linked notes

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