Pentanenitrile, 4,4-dimethyl-3-oxo- → 3-(1,1-Dimethylethyl)-1-(3-quinolinyl)-1H-pyrazol-5-amine

HRID 1696479Notes

Reaction equation

HRID 1696479 reaction equation
Cl.[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH:12][NH2:13])[CH:3]=1.[CH3:14][C:15]([CH3:22])([CH3:21])[C:16](=O)[CH2:17][C:18]#[N:19]>CCO.Cl>[C:15]([C:16]1[CH:17]=[C:18]([NH2:19])[N:12]([C:4]2[CH:3]=[N:2][C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:13]=1)([CH3:22])([CH3:21])[CH3:14]

Participants

5

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 2048560061621-35-0

Product 1

HCID 588514923-(1,1-Dimethylethyl)-1-(3-quinolinyl)-1H-pyrazol-5-amineYield 55%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 1-(quinolin-3-yl)hydrazine hydrochloride (4 g, 20.5 mmol) and 4,4-dimethyl-3-oxo-pentanenitrile (3.6 g, 30 mol) in EtOH (50 mL) and conc. HCl (5 mL) was heated at reflux overnight. After removal of the solvent, the residue was purified by column chromatography to yield 3-t-butyl-1-(quinolin-3-yl)-1H-pyrazol-5-amine (3.0 g, 55% yield). 1H NMR (300 MHz, DMSO-d6): δ 9.16 (d, J=2.4 Hz, 1H), 8.44 (d, J=2.4 Hz, 1H), 8.03 (s, 1H), 8.00 (s, 1H), 7.72 (t, J=7.2 Hz, 1H), 7.64 (t, J=7.2 Hz, 1H), 5.72 (s, 1H), 5.45 (s, 3H), 1.23 (s, 9H).

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-ff2f74685b704055a7b055f5a3be18b2
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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