Sodium Hydroxide → HCID 18919155, compound

HRID 1291316Notes

Reaction equation

HRID 1291316 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[CH:25]=[CH:24][C:11]([CH2:12][N:13]3[C:17]4=[C:18]([Cl:23])[N:19]=[N:20][C:21](Cl)=[C:16]4[CH:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH-:28].[Na+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[CH:25]=[CH:24][C:11]([CH2:12][N:13]3[C:17]4[C:18]([Cl:23])=[N:19][NH:20][C:21](=[O:28])[C:16]=4[CH:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18919103HCID 18919103, compound

Product 1

HCID 18919155HCID 18919155, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

In dioxane (15 ml) was dissolved 1-[4-(4-chlorobenzoyl)benzyl]-4,7-dichloropyrrolo [2,3-d]pyridazine (1.08 g). Then, sodium hydroxide (4.42 g) and water (5 ml) were added and the mixture was refluxed for 69 hours. This reaction mixture was diluted with water (120 ml) and the resulting crystals were collected by filtration. The crystals were purified by silica gel column chromatography (stationary phase 50 g; dichloromethane: ether=1:0-9:1; ethyl acetate: methanol=1:9) to provide 416 mg (yield 40%) of the title compound 1-[4-(4-chlorobenzoyl)benzyl]-4-chloropyrrolo [2,3-d]pyridazin-7(6H)-one(A) and 196 mg (yield 19%) of the title compound 1-[4-(4-chlorobenzoyl)benzyl]-7-chloropyrrolo [2,3-d]pyridazin-4(5H)-one(B).

Workup

  1. temperaturethe mixture was refluxed for 69 hours
  2. filtrationthe resulting crystals were collected by filtration
  3. customThe crystals were purified by silica gel column chromatography (stationary phase 50 g; dichloromethane: ether=1:0-9:1; ethyl acetate: methanol=1:9)

Sources & evidence

ORD record
ord-012056deda354e83b908bcb59a5b38e9
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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