3-Cyanopyridine → HCID 20285824, compound

HRID 268452Notes

Reaction equation

HRID 268452 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].[Na].[CH3:10][NH:11][NH:12][C:13](=O)[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1>CO>[CH3:10][N:11]1[C:1]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)=[N:2][C:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[N:12]1

Participants

5

Reactant 3

HCID 793-CyanopyridineHCID 5360545SodiumHCID 12373457HCID 12373457, compound

Product 1

HCID 20285824HCID 20285824, compoundYield 3.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 3-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-(p-chlorobenzoyl)hydrazine (3.6 g.) in methanol (40 ml.). The reaction mixture is heated at reflux for 5 hours and is then concentrated to an oil which solidifies. After recrystallization from isopropanol, yielding 0.2 g of 1-methyl-3-(p-chlorophenyl)-5-(3-pyridyl)-1,2,4-triazole, m.p. 157°-158°C. is obtained.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 5 hours
  3. concentrationis then concentrated to an oil which
  4. customAfter recrystallization from isopropanol

Sources & evidence

ORD record
ord-2a65ccbdc3de45b4b61087e789ededad
Source dataset
uspto-grants-1976_03
Patent number
US03947577

Reaction notes

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