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

HRID 54429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 54429
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11](=O)[CH3:12])[CH:6]=[CH:7][CH:8]=1.[C:16]1(=[O:23])[CH2:21][CH2:20][CH2:19][C:18](=O)[CH2:17]1.C([O-])(=O)C.[NH4+:28]>C(O)C>[CH3:12][C:11]1[NH:28][C:18]2[CH2:19][CH2:20][CH2:21][C:16](=[O:23])[C:17]=2[CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:15])([F:14])[F:1])[CH:4]=2)[CH:10]=1

Komponenten

5

Edukt 3

HCID 104341,3-CyclohexanedioneHCID 1449341-[3-(Trifluoromethyl)phenyl]but-1-en-3-oneHCID 517165Ammonium Acetate

Produkt 1

HCID 199589122-Methyl-4-(3-trifluoromethylphenyl)-4,6,7,8-tetrahydro-5(1H)-quinoloneAusbeute 39,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4-(3-trifluoromethylphenyl)-3-butene-2-one (4.9 g), 1,3-cyclohexanedione (2.68 g), ammonium acetate (2.65 g) and 75 mL of ethanol were heated at reflux for eight hours and then cooled to room temperature. The solvent was evaporated and the residue was partitioned between water and ethyl acetate. The organic layer was dried, filtered, and evaporated to yield a yellow solid. Recrystallization from ethyl acetate provided the title compound (2.8 g) as an off-white solid; mp 184°-185° C.; NMR: 1.74 (s,3, CH3), 1.87-1.98 (m,2, CH2), 2.13-2.19 (m,2, CH2), 2.42-2.49 (m,2, CH2), 4.50 (d,1, J=4.9, CH), 4.63 (d,1, J=4.9, CH), 7.45 (s,4, Ar), 8.53 (s,1, NH); (CI, CH4) MS: m/z=308(M+1). Analysis for C17H16F3NO: Calculated: C, 66.44; H, 5.25; N, 4.56; Found: C, 65.90; H, 5.33; N, 4.43.

Aufarbeitung

  1. temperaturewere heated
  2. temperatureat reflux for eight hours
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between water and ethyl acetate
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a yellow solid
  9. customRecrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-07b7e2ca3f694977a7cdc93679f65c63
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622964

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