Acetonitrile → 2-methyl-[1,2,4]triazolo[1,5-a]pyridine

HRID 1639824Notes

Reaction equation

HRID 1639824 reaction equation
[I-].[NH2:2][N+:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].[C:11](#[N:13])[CH3:12]>>[CH3:12][C:11]1[N:13]=[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][N:3]2[N:2]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 2733704Pyridinium, 1-amino-, iodide (1:1)

Product 1

HCID 5837152-methyl-[1,2,4]triazolo[1,5-a]pyridineYield 56%

Procedure

To a solution of 1-aminopyridinium iodide (139 g, 626 mmol) in acetonitrile (1.25 L) was added 10% aqueous sodium hydroxide solution (751 mL, 1.88 mmol), and the mixture was stirred at room temperature for 12 hr. Half of the reaction mixture was evaporated under reduced pressure, and the residue was extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give the title compound (47.0 g, yield 56%)

Workup

  1. customHalf of the reaction mixture was evaporated under reduced pressure
  2. extractionthe residue was extracted with dichloromethane
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d02fd7b3891b453a9f41b33a7a3f14eb
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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