Nitric Acid → 5-Bromo-2-methyl-4-nitropyridine 1-oxide

HRID 74594

Reaction equation

HRID 74594 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[Br:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:18])=[N+:15]([O-:17])[CH:16]=1.[OH-].[Na+]>>[Br:10][C:11]1[C:12]([N+:1]([O-:4])=[O:2])=[CH:13][C:14]([CH3:18])=[N+:15]([O-:17])[CH:16]=1

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 8171645-Bromo-2-methylpyridin-1-ium-1-olate

Product 1

HCID 123329085-Bromo-2-methyl-4-nitropyridine 1-oxide

Procedure

6.0 mL nitric acid were added dropwise to 6.0 mL conc. sulphuric acid while cooling with ice and stirring. Then 3.6 g (21 mmol) 5-bromo-2-methylpyridine-1-oxide were added batchwise and the reaction mixture was stirred for 18 h at 60° C. After cooling to RT the reaction mixture was added to ice water and neutralised with 4N aqueous sodium hydroxide solution. The precipitated solid was suction filtered and dried at 50° C.

Workup

  1. temperaturewhile cooling with ice
  2. stirringthe reaction mixture was stirred for 18 h at 60° C
  3. filtrationfiltered
  4. customdried at 50° C.

Sources & evidence

ORD record
ord-682ad6398c654994aac1f32e375e15f1
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

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