Diethyl Ether → Pyridine-4-amidine hydrochloride

HRID 8595

Reaction equation

HRID 8595 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 sodium (0.23 g) in methanol (40 ml) was added 4-cyanopyridine (10.62 g) at room temperature. Stirring was continued for 6 h followed by the addition of ammoniumchloride (5.9 g) and stirring was continued for another 10 h. Then diethylether (120 ml) was added and the precipitate was filtered off after 30 min and washed once with diethylether (20 ml). The product was dried under high vacuum. 4-Amidino-pyridine hydrochloride (14.95 g) 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 diethylether (20 ml)
  5. customThe product was dried under high vacuum

Sources & evidence

ORD record
ord-f98f5a335bf343b985a425cce2db865f
Source dataset
uspto-grants-2006_08
Patent number
US07091201B2

Linked notes

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