4-Cyanopyridine → 2-methyl-4-(3-(pyridin-4-yl)-1H-1,2,4-triazol-5-yl)pyridine

HRID 268448Notes

Reaction equation

HRID 268448 reaction equation
[Na].[C:2]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)#[N:3].[CH3:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][N:20]=1)[C:14]([NH:16][NH2:17])=O>CO>[N:7]1[CH:8]=[CH:9][C:4]([C:2]2[NH:17][N:16]=[C:14]([C:13]3[CH:18]=[CH:19][N:20]=[C:11]([CH3:10])[CH:12]=3)[N:3]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 75064-CyanopyridineHCID 3225492-Methylisonicotinic acid hydrazideHCID 5360545Sodium

Product 1

HCID 203097492-methyl-4-(3-(pyridin-4-yl)-1H-1,2,4-triazol-5-yl)pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
260 °C

Procedure

Sodium (0.4 grams) is added to 4-cyanopyridine (8.3 grams, 0.08 mole) in methanol, and the solution is allowed to stand 30 minutes at room temperature. A suspension of 2-methylisonicotinic acid hydrazide (0.07 mole) in methanol (160 ml.) is added, and the resulting solution is heated at reflux for 30 minutes. After cooling, the intermediate acylamidrazone is collected by filtration. The acyclic intermediate is then heated at 260°C. for 15 minutes, after which the reaction is cooled to room temperature. Upon recrystallization from acetonitrile-water, 5-(4-pyridyl)-3-(2-methyl-4-pyridyl)-1,2,4-triazole is obtained, m.p. 245°-248°C.

Workup

  1. additionis added
  2. temperaturethe resulting solution is heated
  3. temperatureat reflux for 30 minutes
  4. temperatureAfter cooling
  5. filtrationthe intermediate acylamidrazone is collected by filtration
  6. temperatureafter which the reaction is cooled to room temperature
  7. customUpon recrystallization from acetonitrile-water

Sources & evidence

ORD record
ord-73a8b91493344a939b95fabac04cf42b
Source dataset
uspto-grants-1976_03
Patent number
US03947577

Reaction notes

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