Pyridine-2-carbonitrile → HCID 178509724, compound

HRID 431996Notes

Reaction equation

HRID 431996 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[Na].[C:10]([C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([NH:17][NH2:18])=O)#[N:11]>CO>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]1[NH:2][C:15]([C:14]2[CH:19]=[CH:20][CH:21]=[C:12]([C:10]#[N:11])[CH:13]=2)=[N:17][N:18]=1

Participants

5

Reactant 3

HCID 7522Pyridine-2-carbonitrileHCID 5360545SodiumHCID 219426583-Cyanobenzohydrazide

Product 1

HCID 178509724HCID 178509724, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-cyanopyridine (0.18 mL, 1.86 mmol) in methanol (5 mL) was treated with sodium metal (12.8 mg, 0.56 mmol) a stirred at ambient temperature for 1 hour. The reaction mixture was then treated with a solution of 3-cyanobenzhyrazide (0.30 g, 1.86 mmol) in methanol (5 mL) and heated at reflux for 3 hours. The reaction mixture was then concentrated in vacuo. The resulting yellow solid was dissolved in toluene (2 mL) and heated overnight at 175° C. The reaction mixture was concentrated in vacuo. Silica gel chromatography using 2% methanol in dichloromethane afforded 0.12 g (26%) of 2-(2-pyridyl)-5-(3-cyanophenyl)-1,3,4-triazole.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. dissolutionThe resulting yellow solid was dissolved in toluene (2 mL)
  5. temperatureheated overnight at 175° C
  6. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f076a40a9f1f4dffb42658a4817371a1
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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