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

HRID 1525334Notes

Reaction equation

HRID 1525334 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 66.8%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-cyanopyridine (37-a, 100 g, 0.95 mol) in methanol (1.5 L) under nitrogen was added sodium methoxide (2.5 g, 44 mmol). The reaction mixture was stirred at room temperature for 24 h. Then ammonium chloride (53.5 g, 1.0 mol) was added. The mixture was stirred at room temperature for 4 h and the solvent was removed in vacuo. The residue was washed with i-propanol/ethyl acetate=1/10 and dried in vacuo to provide compound 37-b (100 g, 66%).

Workup

  1. stirringThe mixture was stirred at room temperature for 4 h
  2. customthe solvent was removed in vacuo
  3. washThe residue was washed with i-propanol/ethyl acetate=1/10
  4. customdried in vacuo

Sources & evidence

ORD record
ord-de4b9cef105b4fc8801bec1a3ef8646e
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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