(4-Methoxyphenyl)hydrazine → 3-(tert-Butyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-amine

HRID 1696427Notes

Reaction equation

HRID 1696427 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[C:11]([CH2:17][C:18]#[N:19])(=O)[C:12]([CH3:15])([CH3:14])[CH3:13]>CCO.Cl>[C:12]([C:11]1[CH:17]=[C:18]([NH2:19])[N:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 77023(4-Methoxyphenyl)hydrazineHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 111393953-(tert-Butyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-amineYield 82%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of commercially available (4-methoxyphenyl)-hydrazine (17.4 g, 0.1 mol) and commercially available pivaloylacetonitrile (13.8 g, 0.11 mol) in EtOH (500 mL) and conc. HCl (50 mL) was heated at reflux overnight. After removal of the solvent, the residue was purified by column chromatography to afford 3-t-butyl-1-(4-methoxyphenyl)-1H-pyrazol-5-amine (20 g, 82% yield). 1H NMR (300 MHz, DMSO-d6): δ 7.38 (d, J=9.0 Hz, 2H), 6.97 (d, J=9.0 Hz, 2H), 5.32 (s, 1H), 4.99 (brs, 2H), 3.75 (s, 3H), 1.17 (s, 9H); MS (ESI) m/z: 246 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customAfter removal of the solvent
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2d78c9f727f0426a968d6e4318310f2f
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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