Oxygen → 3,5-Diethyl-2-propylpyridine

HRID 614647Notes

Reaction equation

HRID 614647 reaction equation
[CH2:1]([CH:4]1[NH:9][CH:8]([CH2:10][CH2:11][CH3:12])[CH:7]([CH2:13][CH3:14])[CH:6]=N1)[CH2:2][CH3:3].C([O-])(=O)C.[NH4+].O=O>C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:10]([C:8]1[C:7]([CH2:13][CH3:14])=[CH:6][C:1]([CH2:2][CH3:3])=[CH:4][N:9]=1)[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 977Oxygen2×HCID 517165Ammonium AcetateHCID 12508646HCID 12508646, compound

Product 1

HCID 785313,5-Diethyl-2-propylpyridine

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

Into a mixture of 62.9 grams of 2.4-di-n-propyl-5-ethyl-2,3,4,5-tetrahydropyrimidine, 4 grams of ammonium acetate and 4 grams of copper (II) acetate was introduced oxygen gas. Under continuous stirring and introduction of oxygen gas, the mixture was heated for 3 hours at 96°-128° C. The resulting reaction mixture was distilled under diminished pressure. The fraction b20 122°-126° was collected as 37.2 grams (67.8% of theory) of 2-n-propyl-3.5-diethyl pyridine; nuclear magnetic resonance spectrum, no solvent, τ in ppm 1.62 doublet 1H; 2.62 doublet 1H; 7.33 multiplet 6H; 8.20 multiplet 2H; 8.82 triplet and 9.03 triplet 9H.

Workup

  1. customThe resulting reaction mixture
  2. distillationwas distilled under diminished pressure
  3. customThe fraction b20 122°-126° was collected as 37.2 grams (67.8% of theory) of 2-n-propyl-3.5-diethyl pyridine

Sources & evidence

ORD record
ord-b38e669a9e21447eb6cfeab5267322bf
Source dataset
uspto-grants-1979_03
Patent number
US04145545

Reaction notes

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