4-Fluorophenylhydrazine hydrochloride → N-(6-fluoro-1,3,4,9-tetrahydro-2H-carbazol-2-yl)acetamide

HRID 66783

Reaktionsgleichung

Reaktionsgleichung von HRID 66783
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.O=[C:12]1[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C:19](=[O:21])[CH3:20])[CH2:13]1>CC(O)=O>[F:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][C:12]1[CH2:13][CH:14]([NH:18][C:19](=[O:21])[CH3:20])[CH2:15][CH2:16][C:17]2=1

Komponenten

4

Edukt 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 20529251N-(3-oxocyclohexyl)acetamide

Produkt 1

HCID 20529235N-(6-fluoro-1,3,4,9-tetrahydro-2H-carbazol-2-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 0.05 mol of 4-fluorophenylhydrazine hydrochloride and 0.05 mol of N-(3-oxocyclohexyl)acetamide in 75 ml of glacial HOAc was stirred and heated on the steam bath. At 80°-90° an exothermic reaction occurred and the source of heat was removed until the temperature had fallen to 85°. After an additional 4-5 hr at 85°-90°, the warm mixture was poured into H2O and the gummy insolubles triturated until solid. The filtered solid was washed thoroughly with H2O and then with Et2O until the washings were essentially colorless. The crude product was recrystallized from ethanol to give the title compound, mp 209°-210°.

Aufarbeitung

  1. temperatureheated on the steam bath
  2. customAt 80°-90° an exothermic reaction
  3. temperaturethe source of heat
  4. customwas removed until the temperature
  5. customhad fallen to 85°
  6. additionthe warm mixture was poured into H2O
  7. customthe gummy insolubles triturated until solid
  8. washThe filtered solid was washed thoroughly with H2O
  9. customThe crude product was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-336699b17eaf4f308251780c573e07aa
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04343812

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