Pentanenitrile, 4,4-dimethyl-3-oxo- → ethyl 3-(5-amino-3-t-butyl-1H-pyrazol-1-yl)-1-naphthoate

HRID 1696485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696485
Cl.[CH2:2]([O:4][C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]([NH:17][NH2:18])[CH:8]=1)=[O:6])[CH3:3].[CH3:19][C:20]([CH3:27])([CH3:26])[C:21](=O)[CH2:22][C:23]#[N:24]>CCO.Cl>[NH2:24][C:23]1[N:17]([C:9]2[CH:8]=[C:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])[C:16]3[C:11]([CH:10]=2)=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:18]=[C:21]([C:20]([CH3:27])([CH3:26])[CH3:19])[CH:22]=1

Komponenten

5

Edukt 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 67271149Ethyl 3-hydrazinonaphthalene-1-carboxylate hydrochloride

Produkt 1

HCID 58851682ethyl 3-(5-amino-3-t-butyl-1H-pyrazol-1-yl)-1-naphthoateAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3-hydrazinonaphthalene-1-carboxylic acid ethyl ester hydrochloride (1.5 g, 5.6 mmol) and 4,4-dimethyl-3-oxopentanenitrile (875 mg, 7.0 mmol) 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 ethyl 3-(5-amino-3-t-butyl-1H-pyrazol-1-yl)-1-naphthoate (1.8 g, 95% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.74 (d, J=6.3 Hz, 1H), 8.47 (s, 1H), 8.24 (s, 1H), 8.15 (d, J=6.0 Hz, 1H), 7.76 (t, J=5.7 Hz, 1H), 7.71 (t, J=5.7 Hz, 1H), 5.68 (s, 1H), 4.44 (q, J=5.4 Hz, 2H), 1.37 (t, J=5.4 Hz, 3H), 1.30 (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-cb1abdcf015d40cf81e2b326efb74600
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163756B2

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