Acetic Acid → 2-(5-amino-3-phenyl-1H-pyrazol-1-yl)ethan-1-ol

HRID 18488

Reaction equation

HRID 18488 reaction equation
[C:1]([CH2:9][C:10]#[N:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[OH:16][CH2:17][CH2:18][NH:19][NH2:20]>O>[NH2:11][C:10]1[N:19]([CH2:18][CH2:17][OH:16])[N:20]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 80172-HydrazinoethanolHCID 64799Benzoylacetonitrile

Product 1

HCID 21194632-(5-amino-3-phenyl-1H-pyrazol-1-yl)ethan-1-olYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzoylacetonitrile (25 g, 0.17 mol) was suspended in a mixture of 125 mL reagent grade anhydrous alcohol and 20 mL glacial acetic acid. 2-Hydroxyethylhydrazine (14.4 g, 1.1 equiv) dissolved in 35 mL alcohol was added all at once. The mixture was heated at reflux for 4 h, cooled, water was added to make 500 mL total volume and the solution was chilled in a refrigerator overnight. Crystals were filtered cold on a Buchner funnel, washed with cold water and dried on high vacuum to give the desired product (27.2 g, 79%).

Workup

  1. additionwas added all at once
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 4 h
  4. temperaturecooled
  5. temperaturethe solution was chilled in a refrigerator overnight
  6. filtrationCrystals were filtered cold on a Buchner funnel
  7. washwashed with cold water
  8. customdried on high vacuum

Sources & evidence

ORD record
ord-28d09462428f42b9b7c443aa8271cf61
Source dataset
uspto-grants-2010_06
Patent number
US07741355B2

Linked notes

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