O-Xylene → HCID 23153676, compound

HRID 1990776Notes

Reaction equation

HRID 1990776 reaction equation
[CH:1]([NH:3][NH2:4])=O.Cl.C(N(CC)CC)C.C1(C)C(C)=CC=CC=1.Cl[C:22]1[N:27]=[N:26][C:25]([CH3:28])=[C:24]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[CH:23]=1>O>[CH3:36][O:35][C:32]1[CH:33]=[CH:34][C:29]([C:24]2[C:25]([CH3:28])=[N:26][N:27]3[CH:22]=[N:4][N:3]=[C:1]3[CH:23]=2)=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 11130Triethylamine hydrochlorideHCID 12229HydrazinecarboxaldehydeHCID 10585807HCID 10585807, compound

Product 1

HCID 23153676HCID 23153676, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

135 mg (2.25 mmol) of formohydrazide and 310 mg (2.25 mmol) of triethylamine hydrochloride were added to a xylene solution (5 ml) of 352 mg (1.5 mmol) of the obtained 6-chloro-4-(4-methoxyphenyl)-3-methyl-pyridazine, and stirred under reflux for 2 hours. Water was added to the reaction liquid, extracted with ethyl acetate, and the organic layer was washed with saturated saline water. This was dried with anhydrous sodium sulfate, concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=1/2) to obtain 75 mg (yield: 21%) of 7-(4-methoxyphenyl)-6-methyl-[1,2,4]triazolo[4,3-b]pyridazine.

Workup

  1. temperatureunder reflux for 2 hours
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with saturated saline water
  4. dry with materialThis was dried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-02637d4b4dc046919a7fdc028bee6b8d
Source dataset
uspto-grants-2010_01
Patent number
US07645756B2

Reaction notes

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