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

HRID 1696564Notes

Reaction equation

HRID 1696564 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[CH3:11][C:12]([CH3:19])([CH3:18])[C:13](=O)[CH2:14][C:15]#[N:16]>C(O)C.Cl>[C:12]([C:13]1[CH:14]=[C:15]([NH2:16])[N:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=1)([CH3:19])([CH3:18])[CH3:11]

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 (4-methoxy-phenyl)-hydrazine (17.4 g, 0.1 mol) and 4,4-dimethyl-3-oxo-pentanenitrile (13.8 g, 0.11 mol) in ethanol (500 mL) and conc. HCl (50 mL) was heated to reflux overnight. After removal of the solvent, the residue was purified by column chromatography to give 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 (br s, 2H), 3.75 (s, 3H), 1.17 (s, 9H); MS (ESI) m/z: 246 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-d0be7bef18314bc7812e4bc9ddda86b1
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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