Acetic Acid → 5-Chloro-6-(2-methylphenoxy)-3-pyridazinol

HRID 1821681Notes

Reaction equation

HRID 1821681 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[N:4][C:3]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16].C(O)(=[O:19])C.C([O-])(=O)C.[K+]>O>[Cl:1][C:2]1[CH:7]=[C:6]([OH:19])[N:5]=[N:4][C:3]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517044Potassium AcetateHCID 23013971HCID 23013971, compound

Product 1

HCID 1784243955-Chloro-6-(2-methylphenoxy)-3-pyridazinolYield 85.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising 578 mg (2.27 mmol) of 4,6-dichloro-3-(2-methylphenoxy)pyridazine obtained in Example 1 (2), acetic acid (10 mL) and 0.45 g (4.6 mmol) of potassium acetate was refluxed for 5 hours. The reaction mixture was allowed to stand for cooling, and after adding 50 mL of water, the mixture was extracted with ethyl acetate. The organic layers were combined, and washed successively with water and brine. After drying over anhydrous sodium sulfate, the solvent was removed to obtain 461 mg (1.95 mmol, Yield: 85.9%) of 5-chloro-6-(2-methylphenoxy)-3-pyridazinol.

Workup

  1. temperaturefor cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed successively with water and brine
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-a06722ce6e724bbab1669621691045c8
Source dataset
uspto-grants-2009_10
Patent number
US07608563B2

Reaction notes

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