Malononitrile → HCID 22320152, compound

HRID 498002Notes

Reaction equation

HRID 498002 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[NH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[NH2:7]>C(O)C>[NH2:4][C:3]1[N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:7]=[C:1]([CH2:2][C:3]#[N:4])[C:2]=1[C:1]#[N:5]

Participants

4

Reactant 2

HCID 8010MalononitrileHCID 786452-Hydrazinopyridine

Product 1

HCID 22320152HCID 22320152, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of malononitrile (19.8 g, 300 mmol) and 2-hydrazinopyridine (16.4 g, 150 mmol) in ethanol (300 mL) was heated under reflux for 12 hours. The solution was cooled to room temperature, and the resulting crystals were collected by filtration. The crystals were purified by silica gel column chromatography (chloroform to 2% methanol/chloroform) to give the title compound (12.5 g, 37% yield).

Workup

  1. temperatureunder reflux for 12 hours
  2. filtrationthe resulting crystals were collected by filtration
  3. customThe crystals were purified by silica gel column chromatography (chloroform to 2% methanol/chloroform)

Sources & evidence

ORD record
ord-4bbfaf39f6a4459a91bcf5c938943a3a
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

Loading…