Hydrochloric Acid → 3-(tert-Butyl)-1-(quinolin-6-yl)-1H-pyrazol-5-amine

HRID 1930331Notes

Reaction equation

HRID 1930331 reaction equation
Cl.[N:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][NH2:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:14][C:15]([CH3:22])([CH3:21])[C:16](=O)[CH2:17][C:18]#[N:19].Cl>CCO>[C:15]([C:16]1[CH:17]=[C:18]([NH2:19])[N:12]([C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[N:2]=[CH:3][CH:4]=[CH:5]3)[N:13]=1)([CH3:22])([CH3:21])[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 534086886-Hydrazinylquinoline hydrochloride

Product 1

HCID 588517633-(tert-Butyl)-1-(quinolin-6-yl)-1H-pyrazol-5-amineYield 51.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(quinolin-6-yl)hydrazine hydrochloride (4.0 g, 20.5 mmol) and 4,4-dimethyl-3-oxo-pentanenitrile (3.6 g, 30 mol) in EtOH (50 mL) and cone. 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-6-yl)-1H-pyrazol-5-amine (2.8 g, 51% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.84 (d, J=4.2 Hz, 1H), 8.37 (d, J=7.5 Hz, 1H), 8.09 (s, 1H), 8.04 (s, 2H), 7.52 (m, 1H), 5.46 (s, 1H), 5.40 (brs, 2H), 1.29 (s, 9H). MS (ESI) m/z (M+H+): 267.2.

Workup

  1. temperatureat reflux overnight
  2. customAfter removal of the solvent
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2b6aa2da08e04651885f16cb9bdb7fce
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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