Dichloromethane → 6-Chloro-4,5-dimethyl-pyridazine-3-carbonitrile

HRID 1258152Notes

Reaction equation

HRID 1258152 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](I)=[C:6]([CH3:9])[C:7]=1[CH3:8].[Cu](C#N)[C:12]#[N:13].ClCCl>C(#N)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:12]#[N:13])=[C:6]([CH3:9])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 59253660HCID 59253660, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 592536596-Chloro-4,5-dimethyl-pyridazine-3-carbonitrileYield 85.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of D10 (0.225 g, 0.84 mmol), copper cyanide (0.15 g, 1.67 mmol) in acetonitrile (2 ml) was stirred at 160° C. for 20 min., under microwave irradiation. Dichloromethane was then added and the mixture filtered over celite. The solvent was evaporated in vacuo and the residue purified by column chromatography (silica gel; dichloromethane/heptane 1:1 to 7:3) to yield D11 (0.120 g, 85%) as a solid. C7H6ClN3 requires 167. Found 166 (MH−).

Workup

  1. filtrationthe mixture filtered over celite
  2. customThe solvent was evaporated in vacuo
  3. customthe residue purified by column chromatography (silica gel; dichloromethane/heptane 1:1 to 7:3)

Sources & evidence

ORD record
ord-ac41fe7c6bce41ef88ae9044367f75c2
Source dataset
uspto-grants-2013_06
Patent number
US08466153B2

Reaction notes

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