4-Cyanopyridine → HCID 178419986, compound

HRID 596412Notes

Reaction equation

HRID 596412 reaction equation
[Na].[N:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1.[N:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[C:16]([NH:18][NH2:19])=O>CO>[N:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[C:16]1[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=2)[NH:19][N:18]=1

Participants

5

Reactant 3

HCID 75064-CyanopyridineHCID 258796Pyrazine-2-Carboxylic Acid HydrazideHCID 5360545Sodium

Product 1

HCID 178419986HCID 178419986, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
260 °C

Procedure

Sodium (0.4 grams) is added to pyridine-4-carbonitrile (8.3 grams, 0.08 mole) in methanol, and the solution is allowed to stand 30 minutes at room temperature. A suspension of pyrazine carboxylic acid hydrazide (9.6 grams, 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, 3-pyrazinyl-5-(4-pyridyl)-1,2,4-triazole is obtained, m.p. 251°-252.5° 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-45a6cbbfb60c447fa0fe169d0797af38
Source dataset
uspto-grants-1977_03
Patent number
US04011218

Reaction notes

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