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

HRID 729597Notes

Reaction equation

HRID 729597 reaction equation
[CH3:1][O:2][C:3]1([C:6](=O)[CH2:7][C:8]#[N:9])[CH2:5][CH2:4]1.Cl.[C:12]1([CH3:20])[CH:17]=[CH:16][C:15]([NH:18][NH2:19])=[CH:14][CH:13]=1>C(O)C>[CH3:1][O:2][C:3]1([C:6]2[CH:7]=[C:8]([NH2:9])[N:18]([C:15]3[CH:16]=[CH:17][C:12]([CH3:20])=[CH:13][CH:14]=3)[N:19]=2)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 578328203-(1-Methoxy-cyclopropyl)-3-oxo-propionitrile

Product 1

HCID 578328085-(1-methoxy-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-ylamineYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a mixture of 3-(1-methoxy-cyclopropyl)-3-oxo-propionitrile (Preparation 2, 3.55 g, 25.5 mmol) and p-tolylhydrazine hydrochloride (12.15 g, 76.5 mmol) in ethanol (50 mL) at 90° C. in a sealed tube for 18 hours. After removal of the solvent, subject residue to silica gel chromatography eluting with 0-5% methanol in dichloromethane to give the title compound as a yellow solid (3.29 g, 53% yield, ES+(m/z) 244.2 [M+H]).

Workup

  1. temperatureHeat
  2. customAfter removal of the solvent
  3. washeluting with 0-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-595b5acc6a154be0b916a0ded1d5c1a8
Source dataset
uspto-grants-2009_09
Patent number
US07582638B2

Reaction notes

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