2-(2-Chlorophenyl)ethylamine → N-cyano-N'-[2-(2-chlorophenyl)ethyl]-5-hydroxy-3-pyridinecarboximidamide

HRID 1720922Notes

Reaction equation

HRID 1720922 reaction equation
[C:1]([N:3]=[C:4]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([OH:15])[CH:14]=1)OCCC)#[N:2].[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH2:24][NH2:25]>CO>[C:1]([NH:3][C:4]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([OH:15])[CH:14]=1)=[N:25][CH2:24][CH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[Cl:16])#[N:2]

Participants

4

Reactant 2

HCID 831172-(2-Chlorophenyl)ethylamineHCID 22416562propyl N-cyano-5-hydroxy-3-pyridinecarboximidate

Product 1

HCID 22416561N-cyano-N'-[2-(2-chlorophenyl)ethyl]-5-hydroxy-3-pyridinecarboximidamideYield 41.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of propyl N-cyano-5-hydroxy-3-pyridinecarboximidate (0.26 g) in methanol (5 ml) was added 2-(2-chlorophenyl)ethylamine (0.22 g, 1.4 mmol), and the mixture was stirred for 4 hours. After the reaction was completed, the reaction mixture was concentrated under reduced pressure and the residue obtained was extracted with chloroform (50 ml×3). The chloroform layer was washed with water (100 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Wako Gel C-200, 30 g; eluted with chloroform:methanol=50:1) and further crystallized from diethyl ether to give the title compound (0.16 g, 0.53 mmol) as colorless crystals. (Yield starting from 3-cyano-5-hydroxypyridine 15%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue obtained
  3. extractionwas extracted with chloroform (50 ml×3)
  4. washThe chloroform layer was washed with water (100 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (Wako Gel C-200, 30 g; eluted with chloroform:methanol=50:1)
  8. customfurther crystallized from diethyl ether

Sources & evidence

ORD record
ord-4186022adde640f9b238bc8015daa568
Source dataset
uspto-grants-1996_04
Patent number
US05508293

Reaction notes

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