Ammonium Chloride → Pyridine-4-amidine hydrochloride

HRID 1995903

Reaction equation

HRID 1995903 reaction equation
[NH4+:1].[Cl-:2].[C:3](=[NH:13])(OCC)[C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1>C(O)C>[ClH:2].[C:3]([NH2:13])(=[NH:1])[C:4]1[CH:5]=[CH:6][N:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 12263946Ethyl isonicotinimidate

Product 1

HCID 2776844Pyridine-4-amidine hydrochlorideYield 59.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous solution of NH4Cl (26.9 g) is added to a solution of ethyl isonicotinimidate (75.5 g) in ethanol (325 ml). The reaction mixture is heated to reflux for four hours and stirred overnight. A white precipitate is filtered, washed with the mother liquor, dried at 90° C. under house vacuum for 8 hours, yielding 47 g of a white crystalline solid mp. 233°-237° C. The precipitate is dried overnight yielding 44.2 g of the desired hydrochloride, m.p. 237°-240° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for four hours
  3. filtrationA white precipitate is filtered
  4. washwashed with the mother liquor
  5. customdried at 90° C. under house vacuum for 8 hours

Sources & evidence

ORD record
ord-ae906ffa048544caa43cf4791a8cb38d
Source dataset
uspto-grants-1983_09
Patent number
US04406897

Linked notes

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