Pyridine-2-carbonitrile → Pyridine-2-carboximidamide hydrochloride

HRID 487275

Reaction equation

HRID 487275 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[Cl-:9].[NH4+:10]>CO.C[O-].[Na+]>[ClH:9].[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]([NH2:10])=[NH:2]

Participants

5

Reactant 2

HCID 7522Pyridine-2-carbonitrileHCID 25517Ammonium Chloride

Product 1

HCID 12403615Pyridine-2-carboximidamide hydrochlorideYield 94.2%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-cyanopyridine (20.0 g, 0.19 mol) in methanol (300 ml) under argon was added sodium methoxide (0.5 g). The reaction mixture was stirred at room temperature for 24 hours, then ammonium chloride (10.7 g, 0.2 mol) was added. The mixture was stirred at room temperature for 3.5 hours and the solvent was removed in vacuo. The residue was diluted with isopropanol (20 ml) and ether (400 ml) and a solid was collected by filtration to afford 28.2 g (87%) of 2-pyridinecarboxamidine hydrochloride as a white solid, m.p. 141°-142° C. when dried at 40° C. in high vacuum.

Workup

  1. stirringThe mixture was stirred at room temperature for 3.5 hours
  2. customthe solvent was removed in vacuo
  3. additionThe residue was diluted with isopropanol (20 ml) and ether (400 ml)
  4. filtrationa solid was collected by filtration

Sources & evidence

ORD record
ord-8c89d28882ec4d119741ec8fd10c6cd2
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Linked notes

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