4-Cyanopyridine → Pyridine-4-amidine hydrochloride

HRID 1736562Notes

Reaction equation

HRID 1736562 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]#[N:8])=[CH:3][CH:2]=1.C[O-].[Na+].[Cl-:12].[NH4+:13]>CO>[ClH:12].[N:1]1[CH:6]=[CH:5][C:4]([C:7]([NH2:13])=[NH:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 75064-CyanopyridineHCID 25517Ammonium ChlorideHCID 10942334Sodium Methoxide

Product 1

HCID 2776844Pyridine-4-amidine hydrochlorideYield 70.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-pyridinecarbonitrile (370 g, 3.55 mol) and sodium methoxide (20.0 g, 0.37 mol) in methanol (1.7 l) was stirred at room temperature for 1.5 hours, then ammonium chloride (200 g, 3.7 mol) was added. The reaction mixture was stirred for 24 hours, the resulting solid was collected by filtration and the filtrate was evaporated to dryness. The two crops were combined and recrystallized from water to afford 394 g (70%) of 4-pyridinecarboxamidine hydrochloride, m.p. 250°-252° C. (dec.).

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. customthe filtrate was evaporated to dryness
  3. customrecrystallized from water

Sources & evidence

ORD record
ord-c07677ac4f004988b2270e2d0ddfed04
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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