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Methanol → 1-(4-Methoxyphenyl)-3-methyl-1H-pyrazole-5-carboxylic acid

HRID 598799
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 598799
C([O:3][C:4]([C:6]1[N:7]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:8]=[C:9]([CH3:11])[CH:10]=1)=[O:5])C.CO.C1COCC1.[OH-].[Na+]>O>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([N:7]2[C:6]([C:4]([OH:5])=[O:3])=[CH:10][C:9]([CH3:11])=[N:8]2)=[CH:17][CH:16]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 11021617Ethyl 1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-5-carboxylate

Produkt 1

HCID 27695991-(4-Methoxyphenyl)-3-methyl-1H-pyrazole-5-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

To a solution of 2-(4-Methoxy-phenyl)-5-methyl-2H-pyrazole-3-carboxylic acid ethyl ester (400 mg) in a 1:1:1 mixture of MeOH:THF:water was added 10% NaOH (20 mL). The mixture was heated to reflux and the reaction monitored by TLC and HPLC until hydrolysis was complete. The solution was cooled and concentrated under reduced pressure. The residue was acidified with 10% HCl and extracted with EtOAc. The organic fractions were combined and dried over MgSO4 and concentrated under reduced pressure. The resulting solid was used without further purification (Yield 242 mg). LC-MS (C12H12N2O3 calculated 232) m/z 231 (M−H).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customthe reaction monitored by TLC and HPLC until hydrolysis
  4. temperatureThe solution was cooled
  5. concentrationconcentrated under reduced pressure
  6. extractionextracted with EtOAc
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting solid was used without further purification (Yield 242 mg)

Quellen und Nachweise

ORD-Eintrag
ord-550b943d2ae44132823674da5ef70d7d
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07897634B2

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