Ammonium nitrate → 3,5-diethylpyridine

HRID 851321Notes

Reaction equation

HRID 851321 reaction equation
[CH2:1]([CH:3]1[CH2:8][C:7]([CH2:9][CH3:10])=[CH:6]O[CH:4]1OC)[CH3:2].[N+:13]([O-])([O-])=O.[NH4+]>O.C(O)(=O)C.[N+]([O-])(O)=O>[CH2:1]([C:3]1[CH:4]=[N:13][CH:6]=[C:7]([CH2:9][CH3:10])[CH:8]=1)[CH3:2]

Participants

6

Reactant 2

HCID 22985Ammonium nitrateHCID 20502186HCID 20502186, compound

Product 1

HCID 122014443,5-diethylpyridineYield 64%

Reagents, catalysts & solvents 3

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

Procedure

170 parts of 3,5-diethyl-2,3-dihydro-2-methoxy-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 88 parts of ammonium nitrate in 80 parts of water is added. The resulting solution is run into 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 3,5-diethylpyridine is extracted with ether. Distillation gives 87 parts (64% of theory) of 3,5-diethylpyridine of boiling point 92° 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 3,5-diethylpyridine is extracted with ether
  6. distillationDistillation

Sources & evidence

ORD record
ord-441e026812164be19f60c3abb0caaaee
Source dataset
uspto-grants-1983_05
Patent number
US04384120

Reaction notes

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