Nitric Acid → 2-Bromo-4-nitropyridine N-oxide

HRID 583122

Reaction equation

HRID 583122 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8].[N+:9]([O-])([OH:11])=[O:10]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][N+:3]=1[O-:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 3000572-Bromopyridine 1-oxide

Product 1

HCID 39040262-Bromo-4-nitropyridine N-oxideYield 63%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

2-Bromopyridine-N-oxide (28.36 g) was carefully dissolved in concentrated sulphuric acid (43 ml) with stirring. A mixture of concentrated sulphuric acid (65 ml) and concentrated nitric acid (43 ml) was added dropwise, and the mixture refluxed for 3 hours and allowed to cool to room temperature. The mixture was then poured on to ice and the precipitate removed by filtration , washed with water and air dried leaving a fine yellow powder of 2-Bromo-4-nitro-pyridine-N-oxide (14.08 g, 63%), m.p. 145-147° C.

Workup

  1. additionwas added dropwise
  2. temperaturethe mixture refluxed for 3 hours
  3. additionThe mixture was then poured on to ice
  4. customthe precipitate removed by filtration
  5. washwashed with water and air
  6. customdried

Sources & evidence

ORD record
ord-63851fb7d9a54b4d962cf2f391d27b0b
Source dataset
uspto-grants-1999_07
Patent number
US05929082

Linked notes

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