Pyridine-2-carbonitrile → HCID 12799569, compound

HRID 2052193Notes

Reaction equation

HRID 2052193 reaction equation
[Cl-].[NH2:2][N+:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)#[N:10].[OH-].[Na+]>C(O)C.O>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:9]1[N:10]=[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][N:3]2[N:2]=1

Participants

6

Reactant 3

HCID 7522Pyridine-2-carbonitrileHCID 14798Sodium HydroxideHCID 12210597N-amino-pyridinium chloride

Product 1

HCID 12799569HCID 12799569, compoundYield 36.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred and cooled solution of N-amino-pyridinium chloride (26.1 g) and 2-cyanopyridine (31.2 g) in ethanol (100 ml) was added a solution of sodium hydroxide (8.0 g) in water (50 ml) over a period of one hour. The mixture was then left at room temperature for 72 hours, after which time the ethanol was removed in vacuo and the residue extracted with chloroform. The chloroform extract was dried and evaporated. The residue, on recrystallisation from acetone, yielded 14.3 g of 2-(2-pyridyl)-s-triazolo[1,5-a]pyridine.

Workup

  1. customafter which time the ethanol was removed in vacuo
  2. extractionthe residue extracted with chloroform
  3. extractionThe chloroform extract
  4. customwas dried
  5. customevaporated
  6. customThe residue, on recrystallisation from acetone

Sources & evidence

ORD record
ord-16d9ea55baed4811ae5043a64c58ae99
Source dataset
uspto-grants-1980_01
Patent number
US04183741

Reaction notes

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