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

HRID 1930331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1930331
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]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 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 1

HCID 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 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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-2b6aa2da08e04651885f16cb9bdb7fce
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188113B2

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