O-Xylene → HCID 23153692, compound

HRID 1990787Notes

Reaction equation

HRID 1990787 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:23]=[N:24][C:25]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)=[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][C:27]=12>O>[CH3:39][O:38][C:35]1[CH:36]=[CH:37][C:32]([C:25]2[C:26]3[CH:31]=[CH:30][N:29]=[CH:28][C:27]=3[C:22]3[N:23]([CH:1]=[N:3][N:4]=3)[N:24]=2)=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 11130Triethylamine hydrochlorideHCID 12229HydrazinecarboxaldehydeHCID 23153698HCID 23153698, compound

Product 1

HCID 23153692HCID 23153692, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

240 mg (4.0 mmol) of formohydrazide and 551 mg (4.0 mmol) of triethylamine hydrochloride were added to a xylene solution (10 ml) of 543 mg (2.0 mmol) of 4-chloro-1-(4-methoxyphenyl)-pyrido[3,4-d]pyridazine, and then stirred under reflux for 2 hours. Water was added to the reaction liquid, extracted with chloroform, and the organic layer was washed with saturated saline water. This was dried with anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 417 mg of a crude product of 6-(4-methoxyphenyl)-pyrido[3,4-d][1,2,4]triazolo[4,3-b]pyridazine.

Workup

  1. temperatureunder reflux for 2 hours
  2. extractionextracted with chloroform
  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

Sources & evidence

ORD record
ord-b657e60f1eb74a29826d442bd8ff3a2a
Source dataset
uspto-grants-2010_01
Patent number
US07645756B2

Reaction notes

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