Ethanol → ethyl 3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoate

HRID 1392317

Reaktionsgleichung

Reaktionsgleichung von HRID 1392317
Cl.[NH:2]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])[NH2:3].[CH3:13][C:14]([CH3:21])([CH3:20])[C:15](=O)[CH2:16][C:17]#[N:18].[CH2:22](O)[CH3:23]>>[CH2:22]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([N:2]2[C:17]([NH2:18])=[CH:16][C:15]([C:14]([CH3:21])([CH3:20])[CH3:13])=[N:3]2)[CH:5]=1)[CH3:23].[NH2:18][C:17]1[N:2]([C:4]2[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=2)[C:7]([OH:9])=[O:8])[N:3]=[C:15]([C:14]([CH3:21])([CH3:20])[CH3:13])[CH:16]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 128918633-Hydrazinobenzoic acid hydrochloride

Produkt 2

HCID 218672843-(3-tert-butyl-5-amino-1H-pyrazol-1-yl)benzoic acidAusbeute 36 %HCID 21867322ethyl 3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoateAusbeute 40 %

Versuchsvorschrift

A mixture of 3-hydrazino-benzoic acid hydrochloride (200 g, 1.06 mol) and 4,4-dimethyl-3-oxo-pentanenitrile (146 g, 1.167 mol) in ethanol (2 L) was heated to reflux overnight. The reaction solution was evaporated under reduced pressure. The residue was purified by column chromatography to give 3-(5-amino-3-t-butyl-pyrazol-1-yl)-benzoic acid ethyl ester (116 g, 40%) as a white solid together with 3-(5-amino-3-t-butyl-pyrazol-1-yl)-benzoic acid (93 g, 36%). 3-(5-amino-3-t-butyl-pyrazol-1-yl)-benzoic acid and ethyl ester: 1H NMR (DMSO-d6): 8.09 (s, 1 H), 8.05 (brd, J=8.0 Hz, 1 H), 7.87 (br d, J=8.0 Hz, 1 H), 7.71 (t, J=8.0 Hz, 1 H), 5.64 (s, 1 H), 4.35 (q, J=7.2 Hz, 2 H), 1.34 (t, J=7.2 Hz, 3 H), 1.28 (s, 9H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe reaction solution was evaporated under reduced pressure
  4. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-34fa235c70484754a807d4283b3bd9d9
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342037B2

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