Aniline → N-cyano-N'-phenyl-4-pyridinecarboximidamide

HRID 374174Notes

Reaction equation

HRID 374174 reaction equation
[C:1]([N:3]=[C:4]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)OC(C)C)#[N:2].[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO>[C:1]([NH:3][C:4]([C:9]1[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=1)=[N:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)#[N:2]

Participants

4

Reactant 2

HCID 6115AnilineHCID 10012715Isopropyl N-cyano-4-pyridinecarboximidate

Product 1

HCID 19734506N-cyano-N'-phenyl-4-pyridinecarboximidamideYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Isopropyl N-cyano-4-pyridinecarboximidate (0.50 g, 2.6 mmol) was dissolved in methanol (5 ml), and aniline (0.27 g, 2.9 mmol) dissolved in methanol (5 ml) was added. The mixture was stirred at room temperature for 20 minutes. After the reaction was completed, the reaction solution was concentrated under reduced pressure. The residual concentrate was subjected to chromatography on a silica gel column (WAKO GEL C-200, 40 g). Elution with chloroform-methanol (100:1) gave the object compound, which was further crystallized from methanol-diethyl ether to give N-cyano-N'-phenyl-4-pyridinecarboximidamide (0.32 g, 1.4 mmol, yield: 54%) as colorless needles.

Workup

  1. additionwas added
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. concentrationThe residual concentrate
  4. washElution with chloroform-methanol (100:1)
  5. customgave the object compound, which
  6. customwas further crystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-5e66093a7b8944519f1139116249d989
Source dataset
uspto-grants-1992_11
Patent number
US05166347

Reaction notes

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