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

HRID 599307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 599307
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-6059ef3c8fc541c281723c49f1b7122c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897762B2

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