Ammonium nitrate → Pyridine, 3-ethyl-5-methyl-

HRID 851320Notes

Reaction equation

HRID 851320 reaction equation
[CH2:1]([CH:3]1[CH2:8][C:7]([CH3:9])=[CH:6]O[CH:4]1OC)[CH3:2].[N+:12]([O-])([O-])=O.[NH4+]>O.C(O)(=O)C.[N+]([O-])(O)=O>[CH2:1]([C:3]1[CH:4]=[N:12][CH:6]=[C:7]([CH3:9])[CH:8]=1)[CH3:2]

Participants

6

Reactant 2

HCID 22985Ammonium nitrateHCID 20502191HCID 20502191, compound

Product 1

HCID 19901Pyridine, 3-ethyl-5-methyl-Yield 66%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 944Nitric AcidSolventHCID 962WaterSolvent2×

Procedure

156 parts of 3-ethyl-2,3-dihydro-2-methoxy-5-methyl-4H-pyran are dissolved in 25 parts of water, 300 parts of acetic acid and 2 parts of 60 percent strength nitric acid at 22° C. After 15 minutes, a solution of 80 parts of ammonium nitrate in 80 parts of water is added. The resulting solution is added to 800 parts of acetic acid at 110° C. in the course of 20 minutes, whilst stirring. The reaction mixture is left to cool, the acetic acid, water and methanol are distilled off, 200 parts of water are added to the residue and the solution is rendered alkaline with 25 percent strength ammonia solution. The 3-ethyl-5-methyl-pyridine is extracted with ether. Distillation gives 80 parts (66% of theory) of 3-ethyl-5-methyl-pyridine of boiling point 83° C./15 mm Hg.

Workup

  1. waitThe reaction mixture is left
  2. temperatureto cool
  3. distillationthe acetic acid, water and methanol are distilled off
  4. addition200 parts of water are added to the residue
  5. extractionThe 3-ethyl-5-methyl-pyridine is extracted with ether
  6. distillationDistillation

Sources & evidence

ORD record
ord-0cff62c06c3c4360a129f5c71f92d6a4
Source dataset
uspto-grants-1983_05
Patent number
US04384120

Reaction notes

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