Potassium Acetate → 4-(6-Oxo-1,6-dihydro-pyridazin-3-yloxy)-benzoic acid methyl ester

HRID 215837Notes

Reaction equation

HRID 215837 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[N:12]=[N:13][C:14](Cl)=[CH:15][CH:16]=2)=[CH:6][CH:5]=1.C([O-])(=[O:21])C.[K+]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14](=[O:21])[NH:13][N:12]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 606748904-(6-Chloro-pyridazin-3-yloxy)-benzoic acid methyl ester

Product 1

HCID 672971734-(6-Oxo-1,6-dihydro-pyridazin-3-yloxy)-benzoic acid methyl esterYield 75.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-(6-chloro-pyridazin-3-yloxy)-benzoic acid methyl ester (1.0 g, 3.78 mmol) from the previous step and anhydrous potassium acetate (0.526 g, 5.37 mmol) in glacial acetic acid (10 ml) was refluxed for 13 h. The volatiles were evaporated in vacuo and the residue was diluted with dichloromethane (20 ml). The separated solid was collected by filtration, washed with 50% aqueous ethanol (2×5 ml) and water (4×7 ml) and dried to provide 0.7 g (43%) of 4-(6-oxo-1,6-dihydro-pyridazin-3-yloxy)-benzoic acid methyl ester.

Workup

  1. temperaturewas refluxed for 13 h
  2. customThe volatiles were evaporated in vacuo
  3. additionthe residue was diluted with dichloromethane (20 ml)
  4. filtrationThe separated solid was collected by filtration
  5. washwashed with 50% aqueous ethanol (2×5 ml) and water (4×7 ml)
  6. customdried

Sources & evidence

ORD record
ord-40d6a862e36b40eab8fcda3e1585e20f
Source dataset
uspto-grants-2012_06
Patent number
US08193192B2

Reaction notes

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