Diethyl Ether → Pyridine-4-amidine hydrochloride

HRID 1358314Notes

Reaction equation

HRID 1358314 reaction equation
[Na].[C:2]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)#[N:3].[Cl-:10].[NH4+:11].C(OCC)C>CO>[ClH:10].[C:2]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=[NH:11])[NH2:3]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 75064-CyanopyridineHCID 25517Ammonium ChlorideHCID 5360545Sodium

Product 1

HCID 2776844Pyridine-4-amidine hydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.23 g sodium in 40 ml methanol was added 10.62 g 4-cyanopyridine at room temperature. Stirring was continued for 6 h followed by the addition of 5.9 g ammoniumchloride and stirring was continued for another 10 h. Then 120 ml diethylether was added and the precipitate was filtered off after 30 min and washed once with 20 ml of diethylether. The product was dried under highly reduced pressure. 14.95 g 4-amidino-pyridine hydrochloride was obtained as a white powder.

Workup

  1. stirringstirring
  2. waitwas continued for another 10 h
  3. filtrationthe precipitate was filtered off after 30 min
  4. washwashed once with 20 ml of diethylether
  5. customThe product was dried under highly reduced pressure

Sources & evidence

ORD record
ord-83121c0b3d7e444c99628ff5ef5863bd
Source dataset
uspto-grants-2003_07
Patent number
US06596719B1

Reaction notes

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