Pyridine → HCID 178460113, compound

HRID 1708856Notes

Reaction equation

HRID 1708856 reaction equation
[NH2:1][C:2]1[CH:6]([C:7]2[CH:11]=[CH:10][NH:9][N:8]=2)[C:5](=[O:12])[N:4]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([Cl:20])=[CH:15][C:14]=2[Cl:21])[N:3]=1.N1C=CC=CC=1.[N+](C1C=CC=CC=1)([O-])=O.[C:37](Cl)(=[O:40])[CH:38]=[CH2:39].[OH-].[Na+]>O1CCCC1.C(O)(=O)C.O>[Cl:21][C:14]1[CH:15]=[C:16]([Cl:20])[CH:17]=[C:18]([Cl:19])[C:13]=1[N:4]1[C:5](=[O:12])[CH:6]([C:7]2[CH:11]=[CH:10][NH:9][N:8]=2)[C:2]([NH:1][C:37](=[O:40])[CH:38]=[CH2:39])=[N:3]1

Participants

9

Reactant 5

HCID 1049PyridineHCID 7416NitrobenzeneHCID 13140Acryloyl chlorideHCID 14798Sodium HydroxideHCID 178509129HCID 178509129, compound

Product 1

HCID 178460113HCID 178460113, compoundYield 32.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Next, 17 g (0.05 mol) of the 3-amino-1-(2,4,6-trichlorophenyl)-4-pyrazolyl-5-oxo-2-pyrazoline was dissolved in 300 ml qf tetrahydrofuran, to which were added 10 ml (0.13 mol) of pyridine and 1 ml of nitrobenzene. Then, 31.1 g (0.12 mol) of acrylic acid chloride was added under cooling with ice, after which the mixture was stirred for 1.5 hours. Next, 500 ml of water was added, extraction with ethyl acetate was effected, and the extract was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, the residual oil was dissolved in 150 ml of ethanol, and then 60 ml of water containing 3.0 g (0.074 mol) of sodium hydroxide was added at room temperature. After being stirred for 30 min, 3 ml of acetic acid was added to neutralize the solution, the separated oil was extracted with ethyl acetate, the extract was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residual oil was purified by silica gel column chromatography to yield 6.4 g (32%) of the title compound. Melting point: 151° to 154° C.

Workup

  1. temperatureunder cooling with ice
  2. extractionextraction with ethyl acetate
  3. dry with materialthe extract was dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. dissolutionthe residual oil was dissolved in 150 ml of ethanol
  6. stirringAfter being stirred for 30 min
  7. extractionthe separated oil was extracted with ethyl acetate
  8. dry with materialthe extract was dried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residual oil was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1892666bcfea46f497961e37982ce875
Source dataset
uspto-grants-1990_08
Patent number
US04946771

Reaction notes

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