Glyoxylic Acid → 6-(3-Chlorophenyl)-3(2H)-pyridazinone

HRID 1787498Notes

Reaction equation

HRID 1787498 reaction equation
[C:1]([OH:5])(=O)[CH:2]=O.[CH3:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)=O.[NH4+:16].[OH-].O.[NH2:19]N>O>[Cl:15][C:11]1[CH:10]=[C:9]([C:7]2[CH:6]=[CH:2][C:1](=[O:5])[NH:16][N:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 760Glyoxylic AcidHCID 14923Ammonium HydroxideHCID 149331-(3-Chlorophenyl)ethanoneHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 130926206-(3-Chlorophenyl)-3(2H)-pyridazinoneYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

A stirred mixture of glyoxylic acid (4.0 g, 0.054 moles) and 3-chloroacetophenone (25.06 g, 0.162 moles) was heated at 105° C. for 2 hours, then allowed to cool to 40° C. and water (60 ml) was added followed by conc. aq. NH4OH to pH 8. The mixture was extracted with methylene chloride (3×25 ml) to recover the 3-chloroacetophenone. The ammoniacal solution was stirred with hydrazine monohydrate (2.70 g, 0.054 moles) and heated under reflux for 8 hours. The resultant solid was collected by filtration and washed with water to yield the title compound (49%).

Workup

  1. temperatureto cool to 40° C.
  2. extractionThe mixture was extracted with methylene chloride (3×25 ml)
  3. customto recover the 3-chloroacetophenone
  4. temperatureheated
  5. temperatureunder reflux for 8 hours
  6. filtrationThe resultant solid was collected by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-739fed223b044dbcb1895e69bac1d359
Source dataset
uspto-grants-2009_03
Patent number
US07511038B2

Reaction notes

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