4-Cyanopyridine → HCID 21853022, compound

HRID 268449Notes

Reaction equation

HRID 268449 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)#[N:2].[Na].[CH3:10][N:11]([C:13](=O)[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)[NH2:12]>CO>[CH3:10][N:11]1[C:13]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[N:2][C:1]([C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)=[N:12]1

Participants

5

Reactant 3

HCID 75064-CyanopyridineHCID 5360545SodiumHCID 15469977N-Methylpyridine-4-carbohydrazide

Product 1

HCID 21853022HCID 21853022, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 4-cyanopyridine (4.1 grams, 0.04 mole) in methanol (60 ml.) is added sodium (0.2 grams). The resulting solution is allowed to stand at room temperature for 1/2 hour and is then added to a solution of N-methylisonicotinic acid hydrazide (6 grams, 0.04 mole) in methanol (80 ml.). The solution is refluxed for 3 hours and is then concentrated until a solid separates out of solution. The solid is collected by filtration and, upon recrystallization from ethanol, 1-methyl-3,5-di(4-pyridyl)-1,2,4-triazole is obtained, m.p. 168°-170°C.

Workup

  1. temperatureThe solution is refluxed for 3 hours
  2. concentrationis then concentrated until a solid separates out of solution
  3. filtrationThe solid is collected by filtration and, upon recrystallization from ethanol

Sources & evidence

ORD record
ord-bdee25130e0c47e59e1621cf68a15d1a
Source dataset
uspto-grants-1976_03
Patent number
US03947577

Reaction notes

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