Water → HCID 72343106, Verbindung

HRID 910769

Reaktionsgleichung

Reaktionsgleichung von HRID 910769
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:13](=[O:17])[CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][CH:7]=1)=[O:5])[CH3:2].[Br:18][CH:19]=[CH:20][CH2:21]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:18][CH:19]=[CH:20][CH2:21][N:8]1[C:9]2[CH2:10][CH2:11][CH2:12][C:13](=[O:17])[C:14]=2[C:15](=[O:16])[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 52010281,3-DibromopropeneHCID 12876362Ethyl 4,5-dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Produkt 1

HCID 72343106HCID 72343106, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Ethyl-4,5-dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate (714 mg, 3.04 mmol) was suspended in degassed N,N-dimethylformamide (8 mL) and treated with 1,3-dibromo-1-propene (0.364 mL, 3.64 mmol, 1.2 equiv) and potassium carbonate (503 mg, 3.64 mmol, 1.2 equiv). After stirring for 7 hrs at ambient temperature, the mixture was poured into water and extracted three times with ethyl acetate. The combined ethyl acetate extracts were washed once with water and brine, dried with sodium sulfate, filtered and concentrated in vacuo to afforded ethyl 1-[3-bromoprop-2-en-1-yl]-4,5-dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate as a mixture of E- and Z-isomers. Additional compound was obtained by concentration of the aqueous extract in vacuo and extraction of the resulting residue with a mixture of 80% chloroform and 20% methanol (v/v).

Aufarbeitung

  1. extractionextracted three times with ethyl acetate
  2. washThe combined ethyl acetate extracts were washed once with water and brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-55a7999a8f44485ba64ad45c3368732a
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022215B2

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