Hydrochloric Acid → HCID 178428990, compound

HRID 1821707Notes

Reaction equation

HRID 1821707 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[N:13]=[N:14][C:15]([Cl:19])=[CH:16][C:17]=2Cl)=[C:7]([CH3:20])[CH:6]=1)(=O)C.[OH-].[Na+].CS(C)=[O:25].Cl>O1CCOCC1>[Cl:19][C:15]1[N:14]=[N:13][C:12]([O:11][C:8]2[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][C:7]=2[CH3:20])=[C:17]([OH:25])[CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 57464503HCID 57464503, compound

Product 1

HCID 178428990HCID 178428990, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In 1,4-dioxane(1.4 mL) was dissolved 173 mg (0.553 mmol) of 4-[(4,6-dichloro-3-pyridazinyl)oxy]-3-methylphenyl acetate obtained in Example 630(3), 0.7 mL (2.1 mmol) of 3 mol/L sodium hydroxide solution and dimethylsulfoxide (2.8 mL) were added to the solution and the resulting mixture was stirred at room temperature overnight. To the reaction mixture was added 4 mol/L hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed successively with water and brine. After drying over anhydrous magnesium sulfate, the solvent was removed. The obtained residue was purified by preparative thin-layer chromatography (developed by dichloromethane:methanol=36:1) to obtain 66.8 mg of 6-chloro-3-(4-hydroxy-2-methylphenoxy)-4-pyridazinol.

Workup

  1. additionwere added to the solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed successively with water and brine
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. customthe solvent was removed
  6. customThe obtained residue was purified by preparative thin-layer chromatography (developed by dichloromethane:methanol=36:1)

Sources & evidence

ORD record
ord-b0bdffcaca5442359f8172487a75e1cd
Source dataset
uspto-grants-2009_10
Patent number
US07608563B2

Reaction notes

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