Hydrazine hydrate (1:1) → HCID 178434440, Verbindung

HRID 62080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 62080
Cl[C:2]1[C:7]([C:8](=O)[CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.O.[NH2:12][NH2:13]>C(O)CCC>[CH3:9][C:8]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[NH:13][N:12]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 109426973-Acetyl-2-chloropyridine

Produkt 1

HCID 178434440HCID 178434440, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

To a solution of 1-(2-Chloropyridin-3-yl)ethanone (III) (0.311 g, 2 mmol) in n-butanol (10 mL) was added hydrazine hydrate (1.45 mL, 30 mmol). The reaction was refluxed overnight. The solution was cooled and the solvent was evaporated under vacuum. The residue was dissolved in DCM and washed successively by water and brine. The organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to give 3-methyl-1H-pyrazolo[3,4-b]pyridine (IV) as a white solid (192 mg, 1.44 mmol, 72% yield). 1H NMR (CDCl3) δ ppm 2.64 (s, 3H), 7.14 (dd, J=8.01, 4.62 Hz, 1H), 8.14 (dd, J=7.54, 1.88 HZ, 1H), 8.59 (dd, J=4.52, 1.32 HZ, 1H), 11.68 (brs, 1H).

Aufarbeitung

  1. temperatureThe reaction was refluxed overnight
  2. temperatureThe solution was cooled
  3. customthe solvent was evaporated under vacuum
  4. dissolutionThe residue was dissolved in DCM
  5. washwashed successively by water and brine
  6. dry with materialThe organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f0784c782f4f4c3a85bbe4538f84b9de
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09446035B2

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