Diethyl Ether → Pyridine-4-amidine hydrochloride

HRID 2085075Notes

Reaction equation

HRID 2085075 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 high vacuum. 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 high vacuum

Sources & evidence

ORD record
ord-da28e7e3fa0c4b52b0adfc1ff6eea8b0
Source dataset
uspto-grants-2004_04
Patent number
US06720322B2

Reaction notes

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