4-Cyanopyridine → HCID 20309752, compound

HRID 268453Notes

Reaction equation

HRID 268453 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)#[N:2].[Na].[CH3:10][NH:11][NH:12][C:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1>CO>[CH3:10][N:11]1[C:1]([C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)=[N:2][C:13]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[N:12]1

Participants

5

Reactant 3

HCID 75064-CyanopyridineHCID 426763HCID 426763, compoundHCID 5360545Sodium

Product 1

HCID 20309752HCID 20309752, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 4-cyanopyridine (2g.) in methanol (30 ml.) is added sodium (0.1 g.). The solution is allowed to stand 0.5 hours at ambient temperature and is then added to a solution of 1-methyl-2-nicotinoyl-hydrazine (3 g.) in methanol (30 ml.). The reaction mixture is heated 5 hours at reflux and is concentrated to an oil which solidifies. After chromatography on silica gel and recrystallization from acetonitrile 0.8 g. of 1-methyl-3-(3-pyridyl)-5-(4-pyridyl)-1,2,4-triazole melting 132°-133° C is obtained.

Workup

  1. temperatureThe reaction mixture is heated 5 hours
  2. temperatureat reflux
  3. concentrationis concentrated to an oil which
  4. customAfter chromatography on silica gel and recrystallization from acetonitrile 0.8 g

Sources & evidence

ORD record
ord-4721370fffd94e54a82284347d27ec78
Source dataset
uspto-grants-1976_03
Patent number
US03947577

Reaction notes

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