Dichloromethane → 6-Chloropyridazine-3-carbonitrile

HRID 1258146Notes

Reaction equation

HRID 1258146 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](I)=[CH:6][CH:7]=1.[Cu](C#N)[C:10]#[N:11].ClCCl>C(#N)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:10]#[N:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 154188393-Chloro-6-iodopyridazineHCID 178418260HCID 178418260, compound

Product 1

HCID 133828716-Chloropyridazine-3-carbonitrileYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-chloro-6-iodo-pyridazine (CAS 135034-10-5, 5.5 g, 22.9 mmol; Goodman, A. J.; Stanforth, S. P.; Tarbit, B. Tetrahedron (1999), 55 (52), 15067-15070) and copper cyanide (4 g, 44.7 mmol) in acetonitrile (30 ml) was stirred for 30 min. at 160° C., under microwave irradiation (Milestone MW-oven). The mixture was then poured into dichloromethane (200 ml), filtered over celite, and the solvent evaporated in vacuo. The residue was then purified by column chromatography (silica gel; dichloromethane/heptane 1:1 to 7:3) to yield D4 (2.84 g, 89%), as a solid.

Workup

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

Sources & evidence

ORD record
ord-263459d3a9bb4fceade48ac8294c6cc0
Source dataset
uspto-grants-2013_06
Patent number
US08466153B2

Reaction notes

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