Nitric Acid → Pyridine, 2,5-dimethyl-4-nitro-, 1-oxide

HRID 868977Notes

Reaction equation

HRID 868977 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][N+:8]=1[O-:14].[N+:15]([O-])([OH:17])=[O:16]>[OH-].[Na+]>[CH3:6][C:7]1[CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]([CH3:13])=[CH:9][N+:8]=1[O-:14]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 5717732,5-Dimethylpyridin-1-ium-1-olate

Product 1

HCID 146707Pyridine, 2,5-dimethyl-4-nitro-, 1-oxideYield 52%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

To 75 mL of concentrated sulfuric acid at 0° C. was added 2,5-dimethylpyridine N-oxide (10 g, 0.08 mol) dropwise. 5.6 mL of fuming nitric acid (0.13 mol) was added to the mixture. The mixture was heated at 90° C. for 6 h, cooled, poured onto 500 mg ice, and neutralized with 120 mL of 50% sodium hydroxide solution. The solution was extracted with DCM (250 mL×5), and the combined organic phase was dried with anhydrous sodium sulfate and concentrated to give 7.0 g of the crude product as a yellow solid, which was used for the next step without further purification. MS (ESI): m/z 169.1 [M+H]+.

Workup

  1. temperaturecooled
  2. extractionThe solution was extracted with DCM (250 mL×5)
  3. dry with materialthe combined organic phase was dried with anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d8ddf83cfc38406e9e977b79042df784
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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