Sodium Hydroxide → 6-Chloro-2-phenyl-3-(pyridazin-4-yl)imidazo[1,2-b]pyridazine

HRID 1253598Notes

Reaction equation

HRID 1253598 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:17]3[CH:22]=[CH:21][N:20](C(OCC)=O)[N:19]=[CH:18]3)=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[N:7]=1.C1(Cl)C(Cl)=C(Cl)C(=O)C(=O)C=1Cl.[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:17]3[CH:22]=[CH:21][N:20]=[N:19][CH:18]=3)=[C:9]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 73252o-ChloranilHCID 59367705Ethyl 4-[6-chloro-2-phenylimidazo[1,2-b]pyridazin-3-yl]-4H-pyridazine-1-carboxylate

Product 1

HCID 593677046-Chloro-2-phenyl-3-(pyridazin-4-yl)imidazo[1,2-b]pyridazineYield 71.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

22.3 g (58.4 mmol) of ethyl 4-[6-chloro-2-phenylimidazo[1,2-b]pyridazin-3-yl]-4H-pyridazine-1-carboxylate are dissolved in 450 ml of chloroform and 15.1 g (61.3 mmol) of ortho-chloranil are added portionwise. The reaction medium is stirred for 30 minutes at ambient temperature and then poured into a 2N aqueous solution of sodium hydroxide. The product is extracted with chloroform. The organic phase is dried over sodium sulfate and then concentrated under reduced pressure. The dark beige residue is crystallized from a mixture of 80 ml of isopropanol and 60 ml of diisopropyl ether under hot conditions, to give 12.8 g of a beige powder after cooling, isolation by filtration and drying.

Workup

  1. extractionThe product is extracted with chloroform
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe dark beige residue is crystallized from a mixture of 80 ml of isopropanol and 60 ml of diisopropyl ether under hot conditions

Sources & evidence

ORD record
ord-e4c597aa6b224362b9e51ac89fb85208
Source dataset
uspto-grants-2013_06
Patent number
US08455491B2

Reaction notes

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