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

HRID 1270528

Reaktionsgleichung

Reaktionsgleichung von HRID 1270528
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, 1H), 8.05 (brd, J=8.0 Hz, 1H), 7.87 (br d, J=8.0 Hz, 1H), 7.71 (t, J=8.0 Hz, 1H), 5.64 (s, 1H), 4.35 (q, J=7.2 Hz, 2H), 1.34 (t, J=7.2 Hz, 3H), 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-b321b983b7c44ea4aa767ec5c17af5cd
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202257B2

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