Nitric Acid → 4-nitro-3-cyanopyridine N-oxide

HRID 1078246Notes

Reaction equation

HRID 1078246 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([C:7]1[CH:8]=[N+:9]([O-:13])[CH:10]=[CH:11][CH:12]=1)#[N:6].[N+]([O-])([O-])=O.[K+]>>[N+:1]([C:12]1[CH:11]=[CH:10][N+:9]([O-:13])=[CH:8][C:7]=1[C:5]#[N:6])([O-:4])=[O:2]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 24434Potassium NitrateHCID 84686Nicotinonitrile 1-oxide

Product 1

HCID 537498984-nitro-3-cyanopyridine N-oxide

Conditions

Temperature
7.5 °C

Procedure

One hundred fifty mL of stirred 15% fuming nitric acid is cooled to 5-10° C., and 20.4 grams (0.17 mole) of 3-cyanopyridine N-oxide is added portionwise. Upon completion of addition, the reaction mixture is stirred for about 15 minutes, and then 34.4 grams (0.340 mole) of potassium nitrate is added portionwise. Upon completion of addition, the reaction mixture is warmed to about 100° C. where it is stirred for six hours. The reaction mixture is then poured into about 1000 mL of ice-water. The mixture is stirred until the ice melts, and then the resultant solid is collected by filtration. The solid is dried under reduced pressure at about 100° C., yielding 4-nitro-3-cyanopyridine N-oxide.

Workup

  1. additionUpon completion of addition
  2. additionUpon completion of addition
  3. temperaturethe reaction mixture is warmed to about 100° C. where it
  4. stirringis stirred for six hours
  5. filtrationthe resultant solid is collected by filtration
  6. customThe solid is dried under reduced pressure at about 100° C.

Sources & evidence

ORD record
ord-dc3956d1ce084bf1b2e08462d36e9917
Source dataset
uspto-grants-1996_08
Patent number
US05547954

Reaction notes

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