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

HRID 54454

Reaktionsgleichung

Reaktionsgleichung von HRID 54454
[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 C16H16BrNO: 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-d27186ee6e414452abd9a4cf4c8cd414
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622964

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