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

HRID 1525203Notes

Reaction equation

HRID 1525203 reaction equation
C[O-].[Na+].[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)#[N:5].[Cl-:12].[NH4+:13]>CO>[ClH:12].[N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:4]([NH2:13])=[NH:5]

Participants

5

Reactant 3

HCID 7522Pyridine-2-carbonitrileHCID 25517Ammonium ChlorideHCID 10942334Sodium Methoxide

Product 1

HCID 12403615Pyridine-2-carboximidamide hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (2.5 g, 44 mmol) was added to a solution of 2-cyanopyridine (100 g, 0.95 mol) in methanol (1.5 L) under nitrogen. The reaction mixture was stirred at room temperature for 24 hours. Then ammonium chloride (53.5 g, 1 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 ipropanol/ethyl acetate=1/10 and dried in vacuo to provide the product, 1-1-g, (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 ipropanol/ethyl acetate=1/10
  4. customdried in vacuo
  5. customto provide the product, 1-1-g, (100 g, 66%)

Sources & evidence

ORD record
ord-da60fb5a1ddc4059b2945720e336c0fd
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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