Hydrochloric Acid → 1-Phenyl-5-(3-propylphenyl)-4,5-dihydro-1H-pyrazol-3-ylamine

HRID 83514Notes

Reaction equation

HRID 83514 reaction equation
[O-]CC.[Na+].[C:5]1([NH:11][NH2:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:13]([C:16]1[CH:17]=[C:18](/[CH:22]=[CH:23]/[C:24]#[N:25])[CH:19]=[CH:20][CH:21]=1)[CH2:14][CH3:15].C(C1C=C(/C=C\C#N)C=CC=1)CC.Cl>C(O)C.O>[C:5]1([N:11]2[CH:22]([C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([CH2:13][CH2:14][CH3:15])[CH:17]=3)[CH2:23][C:24]([NH2:25])=[N:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7516PhenylhydrazineHCID 2723922Sodium ethoxideHCID 86680356HCID 86680356, compoundHCID 86680357(Z)-3-(3-propylphenyl)acrylonitrile

Product 1

HCID 712877421-Phenyl-5-(3-propylphenyl)-4,5-dihydro-1H-pyrazol-3-ylamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of sodium ethoxide (20 wt % in ethanol, 31 ml) in ethanol (66 ml) was stirred and added dropwise phenylhydrazine (6.4 ml) at room temperature, and then the mixture was stirred for 40 minutes. To this reaction solution was added dropwise a solution of the mixture of (E)-3-(3-propylphenyl)acrylonitrile and (Z)-3-(3-propylphenyl)acrylonitrile (11.1 g) in ethanol (33 ml), and then the mixture was stirred overnight at reflux. This reaction solution was cooled to room temperature, and water (30 ml) was added thereto. Next, pH of the reaction solution was adjusted to 7 by adding a 6M aqueous solution of hydrochloric acid under ice-cooling. This mixed solution was extracted with ethyl acetate, and the resulting organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To the resulting residue was added toluene, and the mixture was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. To the resulting residue was added toluene, and again concentrated under reduced pressure to give a crude product of the titled compound (18.6 g).

Workup

  1. additionTo this reaction solution was added dropwise
  2. stirringthe mixture was stirred overnight
  3. temperatureat reflux
  4. temperaturecooling
  5. extractionThis mixed solution was extracted with ethyl acetate
  6. washthe resulting organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionTo the resulting residue was added toluene
  10. dry with materialthe mixture was dried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. additionTo the resulting residue was added toluene
  13. concentrationagain concentrated under reduced pressure

Sources & evidence

ORD record
ord-dfd95f5b4fa94cc99ba47c368a7d0de0
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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