Phenylhydrazine → 5-Amino-3-methyl-1-phenylpyrazole

HRID 68734

Reaction equation

HRID 68734 reaction equation
O=[C:2]([CH3:6])[CH2:3][C:4]#[N:5].[C:7]1([NH:13][NH2:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)C>[CH3:6][C:2]1[CH:3]=[C:4]([NH2:5])[N:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:14]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 755793-Oxobutyronitrile

Product 1

HCID 708015-Amino-3-methyl-1-phenylpyrazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 1000-mL 3-necked round bottom flask, was placed a solution of 3-oxobutanenitrile (23 g, 277.11 mmol, 1.00 equiv) in ethanol (400 mL), 1-phenylhydrazine (30 g, 277.78 mmol, 1.00 equiv). The resulting solution was heated to reflux overnight in an oil bath. The resulting mixture was then concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10-1:5) to yield 3-methyl-1-phenyl-1H-pyrazol-5-amine as a yellow solid.

Workup

  1. customInto a 1000-mL 3-necked round bottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux overnight in an oil bath
  4. concentrationThe resulting mixture was then concentrated under vacuum

Sources & evidence

ORD record
ord-afa94241a6334361b469a8216d898f9c
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Linked notes

Loading…