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

HRID 54428

Reaktionsgleichung

Reaktionsgleichung von HRID 54428
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=O)[CH3:11])=[CH:4][CH:3]=1.[C:13]1(=[O:20])[CH2:18][CH2:17][CH2:16][C:15](=O)[CH2:14]1.C([O-])(=O)C.[NH4+:25]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:14]3[C:13](=[O:20])[CH2:18][CH2:17][CH2:16][C:15]=3[NH:25][C:10]([CH3:11])=[CH:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 104341,3-CyclohexanedioneHCID 981834-ChlorobenzalacetoneHCID 517165Ammonium Acetate

Produkt 1

HCID 199589244-(4-Chlorophenyl)-2-methyl-4,6,7,8-tetrahydro-5(1H)-quinoloneAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4-(4-Chlorophenyl)-3-butene-2-one (2.83 g), 1.3-cyclohexanedione (1.81 g), and ammonium acetate (2.60 g) were combined in ethanol (125 mL) and heated at reflux for 5.5 h. The solvent was evaporated, and the residue was taken up in water and extracted with ethyl acetate. The combined organic extracts were washed (water, brine), dried, and evaporated to yield a residue which was chromatographed, eluting with hexane:ethyl acetate (1:1) to yield the title compound as a pale yellow solid (1.46 g); mp 184°-187° C.; MS: 273 (M); NMR: 1.73 (s,3, CH3), 1.75-1.98 (m,2, CH2), 2.15 (m,2, CH2), 2.43 (t,2, J=6.0, CH2), 4.39 (d,1, J=4.7, CH), 4.58 (d,1,J=4.8, CH), 7.14 (d,2, J=8.4, Ar), 7.26 (d,2, J=8.4, Ar), 8.48 (s,1, NH); Analysis for C16H16ClNO: Calculated: C, 70.20; H, 5.89; N, 5.12; Found: C, 70.21; H, 5.67; N, 5.02.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 5.5 h
  3. customThe solvent was evaporated
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed (water, brine)
  6. customdried
  7. customevaporated
  8. customto yield a residue which
  9. customwas chromatographed
  10. washeluting with hexane:ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-24b806f6b1af4fd5b832f1988fcf1f78
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622964

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