1,3-Cyclohexanedione → 4-(3-Fluorophenyl)-2-methyl-4,6,7,8-tetrahydro-5(1H)-quinolone

HRID 2209539

Reaktionsgleichung

Reaktionsgleichung von HRID 2209539
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10]1(=[O:17])[CH2:15][CH2:14][CH2:13][C:12](=O)[CH2:11]1.[C:18]([O-])(=O)C.[NH4+].C(O)(=O)C.[NH:27]1[CH2:31][CH2:30]CC1>C(O)C.CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:11]3[C:10](=[O:17])[CH2:15][CH2:14][CH2:13][C:12]=3[NH:27][C:31]([CH3:30])=[CH:18]2)[CH:7]=[CH:8][CH:9]=1

Komponenten

7

Edukt 4

HCID 104341,3-CyclohexanedioneHCID 680093-FluorobenzaldehydeHCID 517165Ammonium AcetateHCID 11040738Pyrrolidine, acetate

Produkt 1

HCID 199589284-(3-Fluorophenyl)-2-methyl-4,6,7,8-tetrahydro-5(1H)-quinoloneAusbeute 0,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 3-fluorobenzaldehyde (7.0 g), 1,3-cyclohexanedione (6.61 g) and ethanol (150 mL) was heated at 70° C. overnight and then cooled to room temperature. Acetone (3.93 g), ammonium acetate (6.52 g) and a solution of pyrrolidine acetate (9.83 g) in ethanol (10 mL) was added and heated at 70° C. for three hours and then cooled to room temperature. The solvent was removed and the residue was partitioned between water and ethyl acetate. The organic layer was dried, filtered, and concentrated in vacuo to obtain an amber oil. Chromatography (methylene chloride/ethyl acetate; 9.0/1.0) and recrystallization from ethanol provided the title compound (0.12 g) as a white solid, mp 216°-218° C.; NMR: 1.73 (s,3, CH3), 1.78-1.90 (m,2, CH2), 2.14-2.19 (m,2, CH2), 2.41-2.46 (m,2, CH2), 4.42 (d,1, J=4.8 CH), 4.61 (d, 1, J=4.8, CH) 6.86-7.00 (m,3, Ar), 7.25 (m,1, Ar), 8.49 (s,1, NH); (CI, CH4) MS: m/z=258(M+1). Analysis for C16H16FNO: Calculated C, 74.69; H, 6.27; N, 5.44; Found: C, 74.39; H, 6.30; N, 5.35.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. temperatureheated at 70° C. for three hours
  3. temperaturecooled to room temperature
  4. customThe solvent was removed
  5. customthe residue was partitioned between water and ethyl acetate
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto obtain an amber oil
  10. customChromatography (methylene chloride/ethyl acetate; 9.0/1.0) and recrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-57dfaf5d2da34371b3c1bb0eba26d63e
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05455253

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