p-Toluidine → N-cyano-N'-(4-methylphenyl)-3-pyridinecarboximidamide

HRID 374147Notes

Reaction equation

HRID 374147 reaction equation
[C:1]([N:3]=[C:4]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)OC(C)C)#[N:2].[CH3:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1>CO>[C:1]([NH:3][C:4]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[N:20][C:19]1[CH:21]=[CH:22][C:16]([CH3:15])=[CH:17][CH:18]=1)#[N:2]

Participants

4

Reactant 2

HCID 7813p-ToluidineHCID 100812013-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl ester

Product 1

HCID 19734526N-cyano-N'-(4-methylphenyl)-3-pyridinecarboximidamideYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Isopropyl N-cyano-3-pyridinecarboximidate (0.50 g, 2.6 mmol) was dissolved in methanol (10 ml), and 4-methylaniline (0.31 g, 2.9 mmol) was added. The mixture was stirred at room temperature for 30 minutes. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the concentrated residue thus obtained was crystallized from dichloromethane-diethyl ether to give the title compound (0.56 g, 2.4 mmol, yield: 90%) as colorless needles.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. customthe concentrated residue thus obtained
  3. customwas crystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-784498108d94480fbed244f33a4a8c72
Source dataset
uspto-grants-1992_11
Patent number
US05166347

Reaction notes

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