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

HRID 2209537

Reaktionsgleichung

Reaktionsgleichung von HRID 2209537
[Br: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>[Br: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 765833-BromobenzaldehydeHCID 517165Ammonium AcetateHCID 11040738Pyrrolidine, acetate

Produkt 1

HCID 199588984-(3-Bromophenyl)-2-methyl-4,6,7,8-tetrahydro-5(1H)-quinoloneAusbeute 8,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A mixture of 3-bromobenzaldehyde (2.0 g), 1,3-cyclohexanedione (1.27 g) and ethanol (30 mL) was heated at reflux for three hours. Acetone (0.75 g), ammonium acetate (1.25 g) and a solution of pyrrolidine acetate (1.89 g) in 4 mL of ethanol was added and refluxing continued overnight. The mixture was cooled, filtered and the filtrate concentrated in vacuo. Chromatography (eluant: methylene chloride/methanol; 98/2) and trituration with ethyl ether provided the title compound (0.28 g) as a yellow solid, mp 187°-191° C.; NMR: 1.73 (s,3, CH3), 1.80-1.90 (m,2, CH2), 2.10-2.18 (m,2, CH2), 2.40-2.45 (m,2, CH2), 4.39 (d,1, J=4.7, CH), 4.59 (d,1, J=4.7, CH), 7.12-7.28 (m,4, Ar), 8.50 (s,1, NH; (CI, CH4) MS: m/z=320(M+1). Analysis for C 16 H16BrNO: Calculated C, 60.39; H, 5.07; N, 4.40; Found: C, 60.19; H, 5.27; N, 4.10.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for three hours
  3. temperaturerefluxing continued overnight
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4804b4886e93422aaf0e71156509eb9a
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05455253

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