3-Acetylpyridine → 1-[[[[1-(3-Pyridinyl)ethylidene]hydrazino]carbonyl]-methyl]pyridinium chloride

HRID 1111124Notes

Reaction equation

HRID 1111124 reaction equation
[CH:1]1[CH:6]=[CH:5][N+:4]([CH2:7][C:8]([NH:10][NH2:11])=[O:9])=[CH:3][CH:2]=1.[Cl-:12].[C:13]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)(=O)[CH3:14]>CO>[Cl-:12].[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:13](=[N:11][NH:10][C:8]([CH2:7][N+:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)=[O:9])[CH3:14])[CH:17]=1

Participants

4

Reactant 2

HCID 95893-AcetylpyridineHCID 70773Pyridinioacetohydrazide chloride

Product 1

HCID 718323881-[[[[1-(3-Pyridinyl)ethylidene]hydrazino]carbonyl]-methyl]pyridinium chlorideYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 5.63 gm (0.03 mole) of Girard's Reagent P in 50 ml of anhydrous methanol is added 3.63 gm (0.03 mole) of 3-acetylpyridine. The solution is refluxed 3 hr and cooled. The solvent is evaporated The residue is slurried in 100 ml of anhydrous ether and filtered. The crude product is recrystallized from absolute ethanol to afford 6.18 gm (71%) of the title compound; mp 237.2° (decomp).

Workup

  1. temperatureThe solution is refluxed 3 hr
  2. temperaturecooled
  3. customThe solvent is evaporated The residue
  4. filtrationfiltered
  5. customThe crude product is recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-41d40e258f2e4ec4a80ef8cf8090796f
Source dataset
uspto-grants-1990_12
Patent number
US04978670

Reaction notes

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