Potassium Carbonate → 6-(Pyridin-4-yl)pyridazin-3(2H)-one

HRID 2426491Notes

Reaction equation

HRID 2426491 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=O)[CH3:2].C(=O)([O-])[O-].[K+].[K+].O.[C:17]([OH:21])(=O)[CH:18]=O.O.[NH2:23][NH2:24]>O.C(O)(=O)C>[N:7]1[CH:8]=[CH:9][C:4]([C:1]2[CH:2]=[CH:18][C:17](=[O:21])[NH:23][N:24]=2)=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 11430Potassium Carbonate2×HCID 142824-AcetylpyridineHCID 24654Hydrazine hydrate (1:1)HCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 27276126-(Pyridin-4-yl)pyridazin-3(2H)-oneYield 64%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

99.5 g 4-Acetylpyridine is added to a cold (10° C.) solution of 222.4 potassium carbonate and 76.3 glyoxylic acid monohydrate in 1 L of water and the solution stirred at room temperature for 2.5 h. After cooling to 0° C., 325 ml of acetic acid are added followed by 58.8 ml hydrazine hydrate, and the resulting solution stirred under reflux for 1.5 h. The solution is then cooled to 0° C., the pH adjusted to 7 with solid K2CO3, the precipitate collected and washed with water and i-PrOH to give 89.27 g (64%) of 6-Pyridin-4-yl-2H-pyridazin-3-one.

Workup

  1. temperatureAfter cooling to 0° C.
  2. stirringthe resulting solution stirred
  3. temperatureunder reflux for 1.5 h
  4. temperatureThe solution is then cooled to 0° C.
  5. customthe precipitate collected
  6. washwashed with water and i-PrOH

Sources & evidence

ORD record
ord-600eb432af46454c970203e441822134
Source dataset
uspto-grants-2011_06
Patent number
US07968546B2

Reaction notes

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