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

HRID 327099Notes

Reaction equation

HRID 327099 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-f70023da539b400388161f2bf0491e6d
Source dataset
uspto-grants-1993_12
Patent number
US05272164

Reaction notes

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