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

HRID 54460

Reaktionsgleichung

Reaktionsgleichung von HRID 54460
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[C:11]1(=[O:18])[CH2:16][CH2:15][CH2:14][C:13](=O)[CH2:12]1.[C:19]([O-])(=O)C.[NH4+].C(O)(=O)C.[NH:28]1[CH2:32][CH2:31]CC1>C(O)C.CC(C)=O>[CH3:19][C:32]1[NH:28][C:13]2[CH2:14][CH2:15][CH2:16][C:11](=[O:18])[C:12]=2[CH:5]([C:4]2[CH:7]=[CH:8][C:9]([F:10])=[C:2]([Cl:1])[CH:3]=2)[CH:31]=1

Komponenten

7

Edukt 4

HCID 104341,3-CyclohexanedioneHCID 517165Ammonium AcetateHCID 5938663-Chloro-4-fluorobenzaldehydeHCID 11040738Pyrrolidine, acetate

Produkt 1

HCID 199589372-Methyl-4-(3-chloro-4-fluorophenyl)-4,6,7,8-tetrahydro-5(1H)-quinoloneAusbeute 2,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 3-chloro-4-fluoro benzaldehyde (2.7 g), 1,3-cyclohexanedione (1.99 g) and 47 mL of ethanol were heated at 50° C. overnight and then cooled to room temperature. Acetone (1.18 g), ammonium acetate (1.97 g) and a premixed solution of pyrrolidine acetate (20.4 mmole) in 5 mL of ethanol were added and heated at 70° C. for three hours and then cooled to room temperature. The solvent was evaporated in vacuo and the residue was partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography (eluant: ether/hexane; 9.0/1.0) over silica gel provided the title compound 0.140 g as a yellow solid, m.p. 164°-167° C. 1H-NMR(300MHz, d6-DMSO): 1.74(s,3H,CH3), 1.81-1.88(m,2H, CH2) 2.15-2.19(m,2H, CH2), 2.41-2.48(m,2H,CH2), 4.41(d, 1H, J=4.8 Hz, CH), 4.60(d,1H, J=4.8(Hz,CH), 7.10-7.28(m,3H, aromatic), 8.54(s,1H, NH); MS (Cl , CH4): 292 (M+1): Analysis for C16H15ClFNO: Calculated: C; 65.87; H; 5.18; N; 4.80: Found: C; 65.67; H; 5.50; N; 4.48.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. temperatureheated at 70° C. for three hours
  3. temperaturecooled to room temperature
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was partitioned between water and ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-51a0f1fd0ae441649769a693c457ffe5
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622964

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