Pyridine-2-carbonitrile → HCID 178478058, compound

HRID 431902Notes

Reaction equation

HRID 431902 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[Na].[Cl:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14]([NH:16][NH2:17])=O>CO>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]1[N:2]=[C:14]([C:13]2[CH:18]=[CH:19][CH:20]=[C:11]([Cl:10])[CH:12]=2)[NH:16][N:17]=1

Participants

5

Reactant 3

HCID 7522Pyridine-2-carbonitrileHCID 742893-ChlorobenzohydrazideHCID 5360545Sodium

Product 1

HCID 178478058HCID 178478058, compoundYield 11.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Using the procedures of Browne et al., Aust. J. Chem., (1975) 28:2543-2546, a solution of 2-cyanopyridine (0.1 mL, 1.00 mmol) in methanol (5 mL) was treated with sodium metal (6.9 mg, 0.30 mmol) and stirred for at ambient temperature for 1 hour. After this time, a solution of 3-chlorobenzhyrazide (0.17 g, 1.0 mmol) in methanol (5 mL) was added and the resulting solution heated at reflux for 3 hours. The reaction mixture was concentrated in vacuo, and the resulting yellow solid (100 mg) dissolved in toluene (2 mL). The mixture was heated at 175° C. for 3 hours and then stirred overnight at ambient temperature. Evaporation of the solvent in vacuo and silica gel chromatography using 1% methanol in dichloromethane afforded 29 mg (11%) of 3-(2-pyridyl)-5-(3-chlorophenyl)-1,2,4-triazole as an off-white solid.

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe resulting yellow solid (100 mg) dissolved in toluene (2 mL)
  5. temperatureThe mixture was heated at 175° C. for 3 hours
  6. stirringstirred overnight at ambient temperature
  7. customEvaporation of the solvent in vacuo and silica gel chromatography

Sources & evidence

ORD record
ord-4171472e225042aab5744c751998bb82
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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