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

HRID 1470312Notes

Reaction equation

HRID 1470312 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 (10-a) (Sigma-Aldrich) (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 hours. Ammonium chloride (53.5 g, 1 mol) was added to the reaction mixture. 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 compound 10-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 ipropanol/ethyl acetate=1/10
  4. customdried in vacuo

Sources & evidence

ORD record
ord-55c8e687970a465391045ee1af97090c
Source dataset
uspto-grants-2015_04
Patent number
US09006433B2

Reaction notes

Loading…