3-Bromophenylhydrazine hydrochloride → 1-(3-Bromophenyl)-3-(tert-butyl)-1H-pyrazol-5-amine

HRID 1696473Notes

Reaction equation

HRID 1696473 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.[CH3:11][C:12]([CH3:19])([CH3:18])[C:13](=O)[CH2:14][C:15]#[N:16]>CCO>[Br:2][C:3]1[CH:4]=[C:5]([N:9]2[C:15]([NH2:16])=[CH:14][C:13]([C:12]([CH3:19])([CH3:18])[CH3:11])=[N:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 337573-Bromophenylhydrazine hydrochlorideHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 184498781-(3-Bromophenyl)-3-(tert-butyl)-1H-pyrazol-5-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (3-bromophenyl)hydrazine hydrochloride (22.2 g, 0.1 mol) and 4,4-dimethyl-3-oxo-pentanenitrile (18.7 g, 0.15 mol) in EtOH (250 mL) was heated at reflux overnight. The reaction was concentrated and the residue purified via column chromatography to yield 2-(3-bromophenyl)-5-t-butyl-2H-pyrazol-3-ylamine as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.85 (s, 1H), 7.68 (d, J=7.6 Hz, 1H), 7.62 (d, J=7.2 Hz, 1H), 7.50 (t, J=8.0 Hz, 1H), 5.62 (s, 1H), 1.27 (s, 9H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction was concentrated
  4. customthe residue purified via column chromatography

Sources & evidence

ORD record
ord-66b15584f05241dab073a3a6b6e621f1
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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