Hydrazine → HCID 76846136, Verbindung

HRID 246034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246034
F[C:2]1[C:9]([F:10])=[C:8]([F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:12][NH2:13]>O1CCOCC1>[F:11][C:8]1[C:9]([F:10])=[C:2]2[C:3]([CH:4]=[N:12][NH:13]2)=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 9321HydrazineHCID 5192262,3,4-Trifluorobenzaldehyde

Produkt 1

HCID 76846136HCID 76846136, VerbindungAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

In a microwave vial 2,3,4-trifluorobenzaldehyde (1.5 g, 9.4 mmol) was dissolved in 1,4-dioxane (6 mL) and hydrazine (6 mL, 191 mmol) was added. The vial was sealed and heated under microwave irradiation at 150° C. for 30 min. The reaction was quenched with water and extracted with EtOAc. The organic layer was washed with brine then dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography with 20% to 50% EtOAc/heptane to provide 664 mg (46%) of 6,7-difluoro-1H-indazole as a light brown powder. 1H NMR (CDCl3, 300 MHz): δ (ppm) 8.10 (d, J=3.4 Hz, 1H), 7.47 (dd, J=8.9, 4.0 Hz, 1H), 7.05 (ddd, J=10.6, 8.9, 6.6 Hz, 1H).

Aufarbeitung

  1. customThe vial was sealed
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialthen dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography with 20% to 50% EtOAc/heptane

Quellen und Nachweise

ORD-Eintrag
ord-80b0c9ebcc3e4c72aea0aa352bb56dfe
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

Notizen zur Reaktion

Wird geladen…