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

HRID 1696479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696479
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]

Komponenten

5

Edukt 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 204856003-Hydrazinylquinoline hydrochloride

Produkt 1

HCID 588514923-(tert-butyl)-1-(quinolin-3-yl)-1H-pyrazol-5-amineAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

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-ff2f74685b704055a7b055f5a3be18b2
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163756B2

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