Acetone → Pyridine-4-amidine hydrochloride

HRID 1829165Notes

Reaction equation

HRID 1829165 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)#[N:2].C[O-].[Na+].CO.[Cl-:14].[NH4+:15].CC(C)=O>CO>[ClH:14].[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)(=[NH:15])[NH2:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 75064-CyanopyridineHCID 25517Ammonium ChlorideHCID 23694274Sodium methanolate methanol

Product 1

HCID 2776844Pyridine-4-amidine hydrochlorideYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Cyanopyridine (50.0 g) was suspended in methanol (50 mL), and 28% sodium methoxide-methanol solution (4.14 mL) was added thereto. After stirring at room temperature for 15 min, ammonium chloride (25.7 g) was added to the mixture. The mixture was stirred at room temperature for 24 hr. Acetone (200 mL) was added to the reaction mixture, and the precipitated solid was collected by filtration to give 4-amidinopyridine hydrochloride (62.8 g) as a white solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 24 hr
  2. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-7cc69d8f7fb74dc2acad7c8209b3d61e
Source dataset
uspto-grants-2006_06
Patent number
US07060722B2

Reaction notes

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