4-Cyanopyridine → Pyridine-4-amidine hydrochloride

HRID 1005889Notes

Reaction equation

HRID 1005889 reaction equation
C[O-].[Na+].[C:4]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)#[N:5].[Cl-:12].[NH4+:13]>CO>[ClH:12].[C:4]([NH2:13])(=[NH:5])[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 75064-CyanopyridineHCID 25517Ammonium ChlorideHCID 10942334Sodium Methoxide

Product 1

HCID 2776844Pyridine-4-amidine hydrochlorideYield 47.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (0.54 g) and 4-cyanopyridine (10.4 g) were combined in anhydrous methanol (100 ml) and stirred at room temperature for 18 h, under a nitrogen atmosphere. Ammonium chloride (5.99 g) was then added, and the mixture heated to reflux for 4 h, under a calcium chloride guard tube. The reaction was cooled, evaporated under reduced pressure, re-suspended in ethanol (120 ml) and heated to reflux for another 15 min. The resultant white precipitate was filtered off, dried, then triturated with ice-cold water and dried under vacuum at 40° C. to yield the title compound as a white solid (7.44 g, 47%). Two further crops were obtained through concentration of the ethanol filtrate (total yield 12.1 g, 77%)

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 4 h, under a calcium chloride guard tube
  3. temperatureThe reaction was cooled
  4. customevaporated under reduced pressure
  5. temperatureheated
  6. temperatureto reflux for another 15 min
  7. filtrationThe resultant white precipitate was filtered off
  8. customdried
  9. customtriturated with ice-cold water
  10. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-1564aa1b2424434aa15e0930696b39b1
Source dataset
uspto-grants-2004_09
Patent number
US06787536B2

Reaction notes

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