Nitric Acid → HCID 59792590, compound

HRID 31677Notes

Reaction equation

HRID 31677 reaction equation
[CH2:1]([C:3]1[C:4]([CH3:10])=[N+:5]([O-:9])[CH:6]=[CH:7][CH:8]=1)[CH3:2].S(=O)(=O)(O)O.[N+:16]([O-])([OH:18])=[O:17]>>[CH2:1]([C:3]1[C:4]([CH3:10])=[N+:5]([O-:9])[CH:6]=[CH:7][C:8]=1[N+:16]([O-:18])=[O:17])[CH3:2]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 597925263-Ethyl-2-methylpyridine1-oxide

Product 1

HCID 59792590HCID 59792590, compoundYield 34.5%

Conditions

Temperature
80 °C

Procedure

While cooling a mixture of 3-ethyl-2-methylpyridine 1-oxide (7.35 g, 53.6 mmol) and sulfuric acid (22.7 g, 231=mmol) in an ice bath, fuming nitric acid (3.64 ml, 87.9 mmol) was added dropwise, which was stirred at 80° C. for 8 hours. The reaction mixture was cooled to room temperature and then poured into ice. The obtained aqueous solution was extracted three times with chloroform. The organic layers were combined, dried over anhydrous magnesium sulfate, filtrated and concentrated to obtain the title compound (3.37 g, yield: 34.5%) as yellow solid.

Workup

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

Sources & evidence

ORD record
ord-88dcb29803eb4c77ad1caedad4d4cf69
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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