Hydrochloric Acid → HCID 178516541, Verbindung

HRID 386378

Reaktionsgleichung

Reaktionsgleichung von HRID 386378
[OH:1][C:2]1[N:6]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1C(OCC)=O.[OH-].[K+].Cl>CO>[C:7]1([N:6]2[C:2]([OH:1])=[CH:3][CH:4]=[N:5]2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 178469976HCID 178469976, Verbindung

Produkt 1

HCID 178516541HCID 178516541, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of ethyl 5-hydroxy-1-(naphthalen-1-yl)-1H-pyrazole-4-carboxylate (480 mg, 1.8 mmol), aqueous potassium hydroxide solution (35%, 2.2 mL, 13.5 mmol) and methanol (5 mL) was heated to reflux for 24 hours. The reaction mixture was then cooled to 0° C., acidified to pH 2 with conc. HCl and refluxed for additional 12 hours to complete decarboxylation. The reaction was then cooled to room temperature and concentrated. The residue was taken up in water and extracted with ethyl acetate, the organic layer washed with water, dried over sodium sulfate and concentrated. Purification by preparative TLC (95% dichloromethane/5% methanol) afforded 1-(naphthalen-1-yl)-1H-pyrazol-5-ol.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. temperaturerefluxed for additional 12 hours
  4. temperatureThe reaction was then cooled to room temperature
  5. concentrationconcentrated
  6. extractionextracted with ethyl acetate
  7. washthe organic layer washed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customPurification by preparative TLC (95% dichloromethane/5% methanol)

Quellen und Nachweise

ORD-Eintrag
ord-a98bd625fd8c4b92bf0a337ae6159102
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372807B2

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