2-Hydrazinopyridine → HCID 178515860, Verbindung

HRID 476200

Reaktionsgleichung

Reaktionsgleichung von HRID 476200
O=[C:2]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][C:4]([O:6]CC)=O.[NH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[NH2:17]>C(O)C>[CH2:9]([C:2]1[CH:3]=[C:4]([OH:6])[N:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:17]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

4

Edukt 2

HCID 786452-HydrazinopyridineHCID 225855Ethyl 3-oxo-4-phenylbutanoate

Produkt 1

HCID 178515860HCID 178515860, VerbindungAusbeute 30,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

Compound 2a (1.03 g, 5.0 mmol) prepared in Step 1 of Example A-1 was charged in a 25 mL round-bottom flask and dissolved in 6 mL of ethanol. A solution of 2-hydrazinopyridine (0.55 g, 5.0 mmol, manufactured by Aldrich) in 5 mL of ethanol at 50° C. was gradually added thereto over 30 minutes, followed by reaction for 1 hour. After completion of the reaction was confirmed by TLC, the reaction solution was concentrated by evaporation, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, and then purified by column chromatography [n-Hex/EtOAc=3/1 (v/v)] to afford a compound of 3-benzyl-1-(pyridin-2-yl)-1H-pyrazol-5-ol (3a).

Aufarbeitung

  1. customfollowed by reaction for 1 hour
  2. concentrationthe reaction solution was concentrated by evaporation
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by column chromatography [n-Hex/EtOAc=3/1 (v/v)]

Quellen und Nachweise

ORD-Eintrag
ord-8c28fcb7cca348d3bd20de67b4acdc17
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637674B2

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