Acetic Acid → 3-Methyl-1-(6-methyl-2-pyridinyl)-1H-pyrazol-5-ylamine

HRID 498067Notes

Reaction equation

HRID 498067 reaction equation
N/[C:2](=[CH:5]\[CH3:6])/[C:3]#[N:4].[NH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=1)[NH2:8].C(O)(=O)C>C(O)C>[CH3:6][C:5]1[CH:2]=[C:3]([NH2:4])[N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=2)[N:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 135904652-Hydrazinyl-6-methylpyridineHCID 86589747Aminocrotononitrile

Product 1

HCID 574177003-Methyl-1-(6-methyl-2-pyridinyl)-1H-pyrazol-5-ylamineYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice-cold solution of aminocrotononitrile (20.5 g, 0.25 mol) and 2-hydrazino-6-methylpyridine (31.0 g, 0.252 mol) in ethanol (200 mL), acetic acid (30 g, 0.5 mol) was added and the mixture was heated under reflux for 2 hours. The reaction solution was allowed to cool to room temperature, and the reaction solvent was concentrated and evaporated under reduced pressure, and water was added to the residue. The solution was made basic by the addition of an aqueous sodium hydroxide solution, and the organic matter was extracted with ethyl acetate. The extract was washed with saturated brine and water, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (ethyl acetate) to give the title compound (41.3 g, 88% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. concentrationthe reaction solvent was concentrated
  4. customevaporated under reduced pressure, and water
  5. additionwas added to the residue
  6. additionThe solution was made basic by the addition of an aqueous sodium hydroxide solution
  7. extractionthe organic matter was extracted with ethyl acetate
  8. washThe extract was washed with saturated brine and water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe residue thus obtained
  12. customwas purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-fff991201c364ef49401195ddebb8cb2
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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