Hydrazine hydrate (1:1) → 3(2H)-Pyridazinone, 6-(3,5-dimethyl-1H-pyrazol-1-yl)-, hydrazone

HRID 27895

Reaction equation

HRID 27895 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([N:8]2[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[N:9]2)=[CH:6][CH:7]=1.O.[NH2:16][NH2:17].O1CCOCC1>O>[NH:16]([C:2]1[N:3]=[N:4][C:5]([N:8]2[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[N:9]2)=[CH:6][CH:7]=1)[NH2:17]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 312751,4-DioxaneHCID 3210733-Chloro-6-(3,5-dimethylpyrazol-1-yl)pyridazine

Product 1

HCID 30539723(2H)-Pyridazinone, 6-(3,5-dimethyl-1H-pyrazol-1-yl)-, hydrazone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 34.2 g. of 3-chloro-6-(3,5-dimethyl-1-pyrazolyl)-pyridazine, 100 ml of 72% hydrazine hydrate and 200 ml of dioxane is stirred at 90°-95° C. for 14 hours, then the mixture is poured into 1 liter of water, extracted three times with 150 ml of chloroform each, and the combined organic phases are dried over magnesium sulphate. After evaporation of the solvent, the residue is recrystallized from isopropanol. Yield: 27 g /80%/; m.p.: 142°-143° C.

Workup

  1. additionA mixture of 34.2 g
  2. extractionextracted three times with 150 ml of chloroform each, and the combined organic phases
  3. dry with materialare dried over magnesium sulphate
  4. customAfter evaporation of the solvent
  5. customthe residue is recrystallized from isopropanol

Sources & evidence

ORD record
ord-4ac82b5535e94a9f90c855027f1f8454
Source dataset
uspto-grants-1980_09
Patent number
US04224325

Linked notes

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