Pyridine-2-carbonitrile → HCID 21853020, compound

HRID 268454Notes

Reaction equation

HRID 268454 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[Na].[CH3:10][NH:11][NH:12][C:13](=O)[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1>CO>[CH3:10][N:11]1[C:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)=[N:2][C:13]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[N:12]1

Participants

5

Reactant 3

HCID 7522Pyridine-2-carbonitrileHCID 417030HCID 417030, compoundHCID 5360545Sodium

Product 1

HCID 21853020HCID 21853020, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 2-cyanopyridine (2 g.) 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-isonicotinoylhydrazine (3 g.) in methanol (50 ml.). The solution is heated at reflux 4 hours and concentrated to a gum. After chromatography on silica gel and recrystallization from acetonitrile-water 450 mg. of 1-methyl-3-(4-pyridyl)-5-(2-pyridyl)-1,2,4-triazole are obtained, melting at 145°-146° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux 4 hours
  3. concentrationconcentrated to a gum
  4. customAfter chromatography on silica gel and recrystallization from acetonitrile-water 450 mg

Sources & evidence

ORD record
ord-6800080501634143aed7cf3653eafb37
Source dataset
uspto-grants-1976_03
Patent number
US03947577

Reaction notes

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