N1-(pyridin-4-yl)ethane-1,2-diamine → (E)-N-(2-nitrocinnamyl)-N'-(4-pyridyl)ethylenediamine

HRID 476997Notes

Reaction equation

HRID 476997 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][CH2:8][CH2:9][NH2:10])=[CH:3][CH:2]=1.[N+:11]([C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[CH:16]=[CH:17][CH2:18]Cl)([O-:13])=[O:12]>C(O)C>[N+:11]([C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1/[CH:16]=[CH:17]/[CH2:18][NH:10][CH2:9][CH2:8][NH:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 14834209N1-(pyridin-4-yl)ethane-1,2-diamineHCID 544529242-Nitro-cinnamyl chloride

Product 1

HCID 14834211(E)-N-(2-nitrocinnamyl)-N'-(4-pyridyl)ethylenediamineYield 29.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 11 g of N-(4-pyridyl)ethylenediamine and 5.3 g of 2-nitrocinnamyl chloride (trans-form) dissolved in 60 ml of ethanol was stirred at room temperature for 30 minutes and then stirred at 50° C. for 90 minutes. The solvent was distilled off under reduced pressure, and 10% aqueous sodium hydroxide was added to the residue and the mixture was extracted with chloroform. After drying of the extract, chloroform was distilled off and the residue was purified by silica gel column chromatography (solvent: chloroform-methanol-triethylamine=20:1:0.1) to give 2.33 g of (E)-N-(2-nitrocinnamyl)-N'-(4-pyridyl)ethyenediamine as a yellow oily substance.

Workup

  1. stirringstirred at 50° C. for 90 minutes
  2. distillationThe solvent was distilled off under reduced pressure, and 10% aqueous sodium hydroxide
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialAfter drying of the extract, chloroform
  6. distillationwas distilled off
  7. customthe residue was purified by silica gel column chromatography (solvent: chloroform-methanol-triethylamine=20:1:0.1)

Sources & evidence

ORD record
ord-53b279c9fa014745a936af0648eec4dd
Source dataset
uspto-grants-1989_12
Patent number
US04886817

Reaction notes

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