Phenylacetonitrile → (6-Chloropyridazin-3-yl)(phenyl)acetonitrile

HRID 1733551Notes

Reaction equation

HRID 1733551 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2-].[Li+].[Cl:12][C:13]1[N:14]=[N:15][C:16](Cl)=[CH:17][CH:18]=1>O1CCCC1>[C:1]1([CH:7]([C:16]2[N:15]=[N:14][C:13]([Cl:12])=[CH:18][CH:17]=2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8794PhenylacetonitrileHCID 24532Lithium amideHCID 673313,6-Dichloropyridazine

Product 1

HCID 5706838(6-Chloropyridazin-3-yl)(phenyl)acetonitrileYield 42.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 8.2 g (0.07 mole) of phenylacetonitrile in 50 ml of dry tetrahydrofuran was added 1.61 g (0.07 mole) of pulverized lithium amide. The mixture was refluxed for 5 hours. To the reaction mixture thereafter cooled were added 8.2 g (0.055 mole) of 3,6-dichloropyridazine and 10 ml of tetrahydrofuran on a water-ice bath. The mixture was then allowed to stand overnight at room temperature. The resulting mixture was neutralized and then distilled to remove the tetrahydrofuran. The residue was chromatographed over silica gel, followed by recrystallization from a mixture of ethanol and isopropyl ether, giving 5.4 g (42.9% yield) of 2-phenyl-2-(6-chloro-3-pyridazinyl)acetonitrile in the form of pale red needles, m.p. 131° C.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. temperatureTo the reaction mixture thereafter cooled
  3. distillationdistilled
  4. customto remove the tetrahydrofuran
  5. customThe residue was chromatographed over silica gel
  6. customfollowed by recrystallization from a mixture of ethanol and isopropyl ether

Sources & evidence

ORD record
ord-1a8b8ade62654cdaa337f309946f4834
Source dataset
uspto-grants-1980_12
Patent number
US04242512

Reaction notes

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