1,2-Cyclohexanedione → HCID 67377466, Verbindung

HRID 877475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877475
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[NH:10]N.[CH2:12]1[CH2:19][C:17](=O)[C:15](=[O:16])[CH2:14][CH2:13]1>CO.CC(O)=O.Cl>[Cl:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]2[C:4]=1[NH:10][C:14]1[C:15](=[O:16])[CH2:17][CH2:19][CH2:12][C:13]2=1

Komponenten

6

Edukt 2

HCID 130061,2-CyclohexanedioneHCID 247210492-Chloro-4-fluorophenylhydrazine hydrochloride

Produkt 1

HCID 67377466HCID 67377466, VerbindungAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To 2-chloro-4-fluoro phenyl hydrazine hydrochloride (0.3 g, 1.5 mmol) in MeOH (2.5 mL), a solution of 1,2-cyclohexadione (0.17 g, 1.5 mmol) in AcOH (2.5 mL) and conc. HCl (1 mL) were added. The resulting mixture was stirred at 60° C. for 12 h, then cooled to room temperature and MeOH was removed in vacuo. Water (25 mL) was added and the reaction mixture was basified with NaHCO3 (pH 8). The crude residue was extracted with EtOAc (2×30 mL). The combined organic extracts were washed with water (50 mL), dried over Na2SO4 and concentrated in vacuo to give the crude material which was purified by silica gel chromatography [EtOAc-hexane (1:19) as eluant] to afford the title compound (0.2 g, 55%). 1H NMR (200 MHz, CDCl3, δ in ppm) 8.84 (bs, 1H), 7.26-7.17 (m, 2H), 2.99-2.93 (t, J=6.0 Hz, 2H), 2.70-2.64 (q, J=7.4, 5.8 Hz, 2H), 2.34-2.21 (m, 2H).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customMeOH was removed in vacuo
  3. additionWater (25 mL) was added
  4. extractionThe crude residue was extracted with EtOAc (2×30 mL)
  5. washThe combined organic extracts were washed with water (50 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give the crude material which
  9. customwas purified by silica gel chromatography [EtOAc-hexane (1:19) as eluant]

Quellen und Nachweise

ORD-Eintrag
ord-726e0f9208c94921abcd92a94f5bffc7
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987319B2

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