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

HRID 2424297Notes

Reaction equation

HRID 2424297 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-4a7e33f74c8f4e028be991a50f86fd48
Source dataset
uspto-grants-2011_06
Patent number
US07964531B2

Reaction notes

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