Methylhydrazine → 1-Methyl-3-phenyl-1H-pyrazol-5-amine

HRID 402477

Reaction equation

HRID 402477 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.[CH3:12][NH:13][NH2:14]>CO>[CH3:12][N:13]1[C:10]([NH2:11])=[CH:9][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:14]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 64799Benzoylacetonitrile

Product 1

HCID 5177791-Methyl-3-phenyl-1H-pyrazol-5-amineYield 71.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of benzoyl acetonitrile (2.0 g, 13.778 mmol) and methyl hydrazine (0.698, 15.156 mmol) in methanol (10 mL) was irradiated under microwave conditions at 110° C. for 90 min. The reaction mixture was cooled to rt and poured into rapidly stirred ice cold water. The obtained solid was collected by filtration, dried under vacuum and triturated with a mixture of pentane-hexane (˜10 mL) to yield a white solid (1.7 g, 71%). [1H-NMR (CDCl3, 300 MHz) δ 7.82-7.65 (m, 2H), 7.45-7.20 (m, 3H), 5.90 (s, 1H), 3.75 (s, 3H), 3.55 (s, 2H); LCMS RtA=0.824 min; [M+H]+=174.1]

Workup

  1. customwas irradiated under microwave conditions at 110° C. for 90 min
  2. additionpoured into rapidly stirred ice cold water
  3. filtrationThe obtained solid was collected by filtration
  4. customdried under vacuum
  5. customtriturated with a mixture of pentane-hexane (˜10 mL)

Sources & evidence

ORD record
ord-13a444bbc6634ce09bcbd8cf08acef13
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Linked notes

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