Nitric Acid → 4-nitro-2-n-propylpyridine-N-oxide

HRID 1421259Notes

Reaction equation

HRID 1421259 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N+:5]=1[O-:10])[CH2:2][CH3:3].[N+:11]([O-])([OH:13])=[O:12].C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O>[N+:11]([C:8]1[CH:7]=[CH:6][N+:5]([O-:10])=[C:4]([CH2:1][CH2:2][CH3:3])[CH:9]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 886162-Propylpyridine 1-oxide

Product 1

HCID 187069664-nitro-2-n-propylpyridine-N-oxideYield 49%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
71 °C

Procedure

A mixture of 2-n-propylpyridine-N-oxide (137.2 g, 1.0 mol) in 200 ml of sulfuric acid (sp.gr. 1.84) was stirred in an ice-salt bath and 320 ml of nitric acid (sp.gr. 1.52) was added. The mixture was carefully heated to 70-72° C. and reacted for 22 hours. The reaction mixture was cooled and poured onto ice and, with stirring, neutralized with portions of sodium carbonate (500 g). The resulting precipitate was collected, washed with water and dried. The dried substance was slurried in 1 liter of dichloromethane and anhydrous sodium sulfate was added. The mixture was filtered and the solvent was evaporated. The yellow residue from evaporation of the dichloromethane solution was dried to afford 89.2 g (49%) of 4-nitro-2-n-propylpyridine-N-oxide. M.p. 89-91° C. 1H-NMR (CDCl3, 200 MHz) δ: 1.10 (t, 3H), 1.70 (sext, 2H), 2.94 (t, 2H), 7.96 (dd, 1H), 8.08 (dd, 1H), 8.30 (dd, 1H).

Workup

  1. addition1.52) was added
  2. customreacted for 22 hours
  3. temperatureThe reaction mixture was cooled
  4. additionpoured onto ice
  5. stirringwith stirring
  6. customThe resulting precipitate was collected
  7. washwashed with water
  8. customdried
  9. additionanhydrous sodium sulfate was added
  10. filtrationThe mixture was filtered
  11. customthe solvent was evaporated
  12. customThe yellow residue from evaporation of the dichloromethane solution
  13. customwas dried

Sources & evidence

ORD record
ord-329f11dead4e41fa9fdec634bf927a6d
Source dataset
uspto-grants-2000_06
Patent number
US06075036

Reaction notes

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