Water → HCID 19436784, compound

HRID 1735009Notes

Reaction equation

HRID 1735009 reaction equation
F[CH:2](F)[C:3]1[CH:7]=[C:6]([O:8][C:9]2[N:10]=[N:11][CH:12]=[C:13]([O:15][CH3:16])[CH:14]=2)[N:5]([CH3:17])[N:4]=1.ClCCl.[Cl-].[Al+3].[Cl-].[Cl-].[OH2:26]>>[CH3:16][O:15][C:13]1[CH:14]=[C:9]([O:8][C:6]2[N:5]([CH3:17])[N:4]=[C:3]([CH:2]=[O:26])[CH:7]=2)[N:10]=[N:11][CH:12]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 6451240Aluminum(III) Chloride2×HCID 19436780HCID 19436780, compound

Product 1

HCID 19436784HCID 19436784, compoundYield 12%

Procedure

3-[[3-(Difluoromethyl)-1-methyl-1H-pyrazol-5-yl]oxy]-5-methoxypyridazine (Compound No. 45, 4.5 g, 0.017 mole) and dichloromethane (80 mL) were stirred and cooled with a water bath while aluminum chloride (4.3 g, 0.031 mole, (note: this aluminum chloride was old and wet) was added and the mixture was then stirred at room temperature for 5 hours. The mixture was poured into cold water and the aqueous phase washed three times with dichloromethane. The pH of the aqueous phase was adjusted to 4, using 10% sodium hydroxide; and the product was extracted with ethyl acetate. The extracts were dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel to give 5-[(5-methoxy-3-pyridazinyl)oxy]-1-methyl-1H-pyrazole-3-carboxaldehyde (0.50 g, 12% yield) as white solid.

Workup

  1. additionwet) was added
  2. washthe aqueous phase washed three times with dichloromethane
  3. extractionand the product was extracted with ethyl acetate
  4. dry with materialThe extracts were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-977dfd1dafd347549efd6985c29ff655
Source dataset
uspto-grants-1996_07
Patent number
US05536701

Reaction notes

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