4-Methylphenylhydrazine monohydrochloride → 5-(1-methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-ylamine

HRID 729601Notes

Reaction equation

HRID 729601 reaction equation
[CH3:1][C:2]1([C:5](=O)[CH2:6][C:7]#[N:8])[CH2:4][CH2:3]1.Cl.[C:11]1([CH3:19])[CH:16]=[CH:15][C:14]([NH:17][NH2:18])=[CH:13][CH:12]=1>C(O)C>[CH3:1][C:2]1([C:5]2[CH:6]=[C:7]([NH2:8])[N:17]([C:14]3[CH:15]=[CH:16][C:11]([CH3:19])=[CH:12][CH:13]=3)[N:18]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 133930463-(1-Methylcyclopropyl)-3-oxopropanenitrile

Product 1

HCID 685368275-(1-methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-ylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat to reflux a solution of 3-(1-methyl-cyclopropyl)-3-oxo-propionitrile (60 g, 487.2 mmol) and p-tolyl-hydrazine hydrochloride (78 g, 478.2 mmol) in ethanol (975 mL) for 4 hours. Evaporate the solvent and dissolve the remaining solid in water. Increase pH of the solution to pH 8 using a 1.0 N solution of sodium hydroxide. Filter the precipitate to obtain 5-(1-methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-ylamine as a white solid. 1H NMR (DMSO): 7.39 (d, J=8 Hz, 2H), 7.22 (d, J=8 Hz, 2H), 5.12 (s, 2H), 2.31 (s, 3H), 1.30 (s, 3H), 0.80 (q, J=4 Hz, 2H), 0.61 (q, J=4 Hz, 2H).

Workup

  1. temperatureHeat
  2. customEvaporate the solvent
  3. dissolutiondissolve the remaining solid in water
  4. temperatureIncrease pH of the solution to pH 8
  5. filtrationFilter the precipitate

Sources & evidence

ORD record
ord-678eeae911044185b2d5dd00c4f55c5b
Source dataset
uspto-grants-2009_09
Patent number
US07582638B2

Reaction notes

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