O-Xylene → 6-(4-Methoxyphenyl)-3-phenyl-[1,2,4]triazolo[3,4-a]phthalazine

HRID 1990782Notes

Reaction equation

HRID 1990782 reaction equation
[C:1]([NH:9][NH2:10])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N(CC)CC)C.C1(C)C(C)=CC=CC=1.Cl[C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)=[N:30][N:29]=1>O>[CH3:45][O:44][C:41]1[CH:42]=[CH:43][C:38]([C:31]2[C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:28]3=[N:10][N:9]=[C:1]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[N:29]3[N:30]=2)=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 11130Triethylamine hydrochlorideHCID 11955BenzoylhydrazineHCID 27723901-Chloro-4-(4-methoxyphenyl)phthalazine

Product 1

HCID 19806306-(4-Methoxyphenyl)-3-phenyl-[1,2,4]triazolo[3,4-a]phthalazineYield 99.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

163 mg (1.2 mmol) of benzohydrazide and 165 mg (1.2 mmol) of triethylamine hydrochloride were added to a xylene solution (5 ml) of 271 mg (1.0 mmol) of the obtained 1-chloro-4-(4-methoxyphenyl)-phthalazine, and then 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, and concentrated under reduced pressure to obtain 350 mg of a crude product of 6-(4-methoxyphenyl)-3-phenyl-[1,2,4]triazolo[3,4-a]phthalazine.

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

Sources & evidence

ORD record
ord-99c7ea2fee2d44129dd0051ae79afdc9
Source dataset
uspto-grants-2010_01
Patent number
US07645756B2

Reaction notes

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