Methanol → 5-Amino-1-(2-hydroxyethyl)-3-methyl-4-phenylpyrazole

HRID 1783302

Reaction equation

HRID 1783302 reaction equation
[C:1]([CH:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:5]#[N:6])(=O)[CH3:2].[NH:13]([CH:15](O)[CH3:16])[NH2:14].C[OH:19]>>[NH2:6][C:5]1[N:13]([CH2:15][CH2:16][OH:19])[N:14]=[C:1]([CH3:2])[C:4]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 20547Alpha-phenylacetoacetonitrileHCID 19013750Hydrazinoethanol

Product 1

HCID 177240495-Amino-1-(2-hydroxyethyl)-3-methyl-4-phenylpyrazole

Procedure

α-Acetylphenylacetonitrile (10 g) was dissolved in methanol (100 mL), and hydrazinoethanol (5.3 g) was added, and the mixture was heated under reflux for 4 hrs. After the completion of the reaction, the solvent was evaporated. The obtained residue was subjected to silica gel column chromatography, and the fraction eluted with chloroform:methanol=40:1 was concentrated to give 5-amino-1-(2-hydroxyethyl)-3-methyl-4-phenylpyrazole (11.4 g) as white crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. customAfter the completion of the reaction
  4. customthe solvent was evaporated
  5. washthe fraction eluted with chloroform
  6. concentrationmethanol=40:1 was concentrated

Sources & evidence

ORD record
ord-60683cf36ac5418d8f27950efd500f7f
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Linked notes

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