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

HRID 31613

Reaction equation

HRID 31613 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][N+:3]=1[O-:10].S(=O)(=O)(O)O.[N+:16]([O-])([OH:18])=[O:17]>>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:16]([O-:18])=[O:17])[C:5]([CH3:9])=[CH:4][N+:3]=1[O-:10]

Participants

4

Reactant 3

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

Product 1

HCID 112176114-Nitro-2,3,5-trimethylpyridine, 1-oxideYield 93.1%

Conditions

Temperature
80 °C

Procedure

The 2,3,5-trimethylpyridine1-oxide (11.0 g, 80.2 mmol) obtained in the step (11b) was mixed with sulfuric acid (34.1 g, 348 mmol). After fuming nitric acid (5.50 ml, 133 mmol) was added dropwise to this mixture at room temperature, the mixture was stirred at 80° C. for 9 hours. The reaction mixture was cooled to room temperature and thereafter poured into ice. The obtained aqueous solution was extracted with chloroform three times. Organic layers were combined and dried over anhydrous magnesium sulfate, filtered and concentrated to obtain the title compound (13.6 g, yield: 93.1%) as a yellow solid.

Workup

  1. additionwas added dropwise to this mixture at room temperature
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additionpoured into ice
  4. extractionThe obtained aqueous solution was extracted with chloroform three times
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e3543f00d349451ab8e265392c8c426b
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Linked notes

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