4-Methylphenylhydrazine monohydrochloride → 3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amine

HRID 1897504Notes

Reaction equation

HRID 1897504 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[C:11]([CH2:17][C:18]#[N:19])(=O)[C:12]([CH3:15])([CH3:14])[CH3:13]>CO>[C:12]([C:11]1[CH:17]=[C:18]([NH2:19])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:10])=[CH:3][CH:4]=2)[N:9]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 29741323-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amineYield 116%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of p-tolyl-hydrazine hydrochloride (15.86 g, 100 mmol) and pivaloylacetonitrile (17.9 g, 143 mmol) dissolved in MeOH (65 mL) was heated to reflux for 18 hours under N2 atmosphere. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was triturated with ether and collected by filtration. The solid was dried under high vacuum to provide 26.6 g of white solid (99% yield).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours under N2 atmosphere
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with ether
  5. filtrationcollected by filtration
  6. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-aec70d1f5e6f4d57a8dd1ab9c564d4d0
Source dataset
uspto-grants-2013_08
Patent number
US08518983B2

Reaction notes

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