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

HRID 2112209Notes

Reaction equation

HRID 2112209 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-f410e75ce5bb4947aebbaf0eef311e87
Source dataset
uspto-grants-2009_04
Patent number
US07521447B2

Reaction notes

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