Pentanenitrile, 4,4-dimethyl-3-oxo- → 3-(tert-Butyl)-1-(quinolin-6-yl)-1H-pyrazol-5-amine

HRID 1696477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696477
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]>CCO.Cl>[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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 588517633-(tert-Butyl)-1-(quinolin-6-yl)-1H-pyrazol-5-amineAusbeute 51,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

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 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-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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-03cd5dda7af74f948854e320d3eec3f4
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163756B2

Notizen zur Reaktion

Wird geladen…