Ethyl Acetate → Ethyl 1-bromo-4-oxo-4H-quinolizine-3-carboxylate

HRID 48907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 48907
[O:1]=[C:2]1[N:11]2[C:6]([CH:7]=[CH:8][CH:9]=[CH:10]2)=[CH:5][CH:4]=[C:3]1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[Br:17]Br.C(OCC)(=O)C>C(O)(=O)C>[Br:17][C:5]1[CH:4]=[C:3]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2](=[O:1])[N:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[CH:10]2

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 24408BromineHCID 4615166Ethyl 4-oxo-4H-quinolizine-3-carboxylate

Produkt 1

HCID 20634149Ethyl 1-bromo-4-oxo-4H-quinolizine-3-carboxylateAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl 4-oxo-4H-quinolizine-3-carboxylate (1) (2.33 g, 10.7 mmol) in 20 ml acetic acid was rapidly added a solution of bromine (1.9 g, 12 mmol) in 10 ml acetic acid. The reaction was complete after 5 min, as indicated by thin layer chromatography (ethyl acetate). The solvent was evaporated in vacuo and the remaining yellow solid was dissolved in 20 ml dichloromethane. To this solution, silica gel (3 g) was added and the solvent was evaporated in vacuo. The silica gel was poured on a prepacked column and eluted with ethyl acetate to give ethyl 1-bromo-4-oxo-4H-quinolizine-3-carboxylate (9) as a bright yellow solid (2.1 g, 71%). M.p. 156-158° C. 1H NMR (δ, CDCl3): 1.43 (t, J=7 Hz, 3H), 4.43 (q, J=7 Hz, 2H), 7.03 (dd, J=7 Hz, J=7 Hz, 1H), 7.30 (dd, J=7 Hz, 2H), 7.80 (dd, J=7 Hz, J=7 Hz, 1H), 8.63 (s, 1H), 9.49 (d, J=7 Hz). MS: m/z 294.9839; required for C12H10BrNO3: 294.9843.

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe remaining yellow solid was dissolved in 20 ml dichloromethane
  3. additionTo this solution, silica gel (3 g) was added
  4. customthe solvent was evaporated in vacuo
  5. additionThe silica gel was poured on a prepacked column
  6. washeluted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d3178d8e91d04267aa1ceb80d6bc1c57
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706528B2

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