Acrylonitrile → 2-(2'-Cyanoethyl)-4-cyano-5,6-diphenyl-3-(2H)-pyridazinone

HRID 463969Notes

Reaction equation

HRID 463969 reaction equation
[C:1]([C:3]1[C:4](=[O:21])[NH:5][N:6]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)#[N:2].[C:22](#[N:25])[CH:23]=[CH2:24]>N1C=CC=CC=1.O>[C:22]([CH2:23][CH2:24][N:5]1[C:4](=[O:21])[C:3]([C:1]#[N:2])=[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:6]1)#[N:25]

Participants

5

Reactant 2

HCID 7855AcrylonitrileHCID 957574-Pyridazinecarbonitrile, 2,3-dihydro-3-oxo-5,6-diphenyl-

Product 1

HCID 135335002-(2'-Cyanoethyl)-4-cyano-5,6-diphenyl-3-(2H)-pyridazinone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

4.0 grams (0.0146 mole) of 4-cyano-5,6-diphenyl-3-(2H)-pyridazinone was dissolved in 40 mls of pyridine along with 10 mls of distilled water. 2 mls of acrylonitrile was added into this solution and the mixture heated to reflux for 2 hours. The solution was cooled and the solvent distilled at reduced pressure. The residual solid was recrystallized from ethyl alcohol to give 2 grams (42%) yield of a white solid which melted at 160°-161° C. The infrared spectrum showed the C-C band at 3.3μ, the nitrile group at 4.5μ, and the carboxy groups for an amide at 6.0μ.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe solution was cooled
  4. distillationthe solvent distilled at reduced pressure
  5. customThe residual solid was recrystallized from ethyl alcohol
  6. customto give 2 grams (42%) yield of a white solid which melted at 160°-161° C

Sources & evidence

ORD record
ord-6c90b97b584245fdbb387c516144c828
Source dataset
uspto-grants-1985_10
Patent number
US04545810

Reaction notes

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