Water → 3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenol

HRID 221867

Reaktionsgleichung

Reaktionsgleichung von HRID 221867
Cl.[C:2]([C:6]1[CH:7]=[C:8]([NH2:19])[N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17]C)[CH:12]=2)[N:10]=1)([CH3:5])([CH3:4])[CH3:3].Cl.[NH+]1C=CC=CC=1.O>CCOC(C)=O>[NH2:19][C:8]1[N:9]([C:11]2[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=2)[N:10]=[C:6]([C:2]([CH3:5])([CH3:4])[CH3:3])[CH:7]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 21584435Pyridinium hydrochlorideHCID 670222745-tert-butyl-2-(3-methoxy-phenyl)-2H-pyrazol-3-ylamine hydrochloride

Produkt 1

HCID 595579663-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenolAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
195 °C

Versuchsvorschrift

In a 500 mL round bottom flask was added 5-tert-butyl-2-(3-methoxy-phenyl)-2H-pyrazol-3-ylamine hydrochloride (8.42 g, 30 mmol) and pyridinium hydrochloride (13.8 g, 120 mmol). The reaction mixture was heated neat at 195° C. with stirring for 3 h. The mixture was cooled to room temperature, water (300 mL) and EtOAc (300 mL) were added, and then the organic phase was washed with saturated aq NaHCO3 and brine, dried (Na2SO4) and concentrated at reduced pressure. The residue was purified by MPLC (80:20 hexane/EtOAc) to give the product 3-(5-amino-3-tert-butyl-pyrazol-1-yl)-phenol (1.3 g, 19%). 1H-NMR (DMSO-d6) δ 7.20 (t, 1H), 7.00 (m, 2H), 6.50 (d, 1H), 5.30 (s, 1H), 5.10 (bs, 2H), 1.30 (s, 9H); MS LC-MS [M+H]+=232.2, RT=0.57 min.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. washthe organic phase was washed with saturated aq NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was purified by MPLC (80:20 hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-28fb7d9993e1430b91707776875de31c
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207166B2

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