Nitric Acid → 4-Nitro-2,3,5-trimethylpyridine, 1-oxide

HRID 1379085Notes

Reaction equation

HRID 1379085 reaction equation
[N+:1]([O-:4])(O)=[O:2].OS(O)(=O)=O.[CH3:10][C:11]1[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][N+:12]=1[O-:19].[OH-].[Na+]>O>[N+:1]([C:15]1[C:14]([CH3:18])=[CH:13][N+:12]([O-:19])=[C:11]([CH3:10])[C:16]=1[CH3:17])([O-:4])=[O:2]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 104869072,3,5-Trimethyl-1-oxidopyridin-1-ium

Product 1

HCID 112176114-Nitro-2,3,5-trimethylpyridine, 1-oxideYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled solution of fuming HNO3 (50 ml) and conc. H2SO4 (50 ml) in an ice bath was added 2,3,5-trimethylpyridine-N-oxide (35.67 g) and the reaction mixture was stirred at 40°-50° C. for 18 h. After which time, the reaction was cooled to rt, poured into water/crushed ice (250 ml), alkalized with NaOH pellets and extracted with CH2 Cl2 (3×100 ml). The extracts were combined and washed with sat. NaCl (1×50 ml), dried (MgSO4) and the solvent removed in vacuo to give 4-nitro-2,3,5-trimethyl-pyridine-N-oxide (45.5 g, 96%) as an orange solid; mp 69°-71° C. (ether), orange plates.

Workup

  1. extractionextracted with CH2 Cl2 (3×100 ml)
  2. washwashed with sat. NaCl (1×50 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a90dbf3627aa4a548fa1981b6fb0b242
Source dataset
uspto-grants-1997_09
Patent number
US05670526

Reaction notes

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