Hydrochloric Acid → HCID 67770344, Verbindung

HRID 373775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 373775
[Na].[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[Cl:13])[NH:9][C:8](=[O:14])[CH:7]=[N:6]2.Br[CH:16]([CH2:22][CH2:23][CH2:24][CH3:25])[C:17]([O:19][CH2:20][CH3:21])=[O:18].Cl>C(O)C>[CH2:20]([O:19][C:17]([CH2:16][CH2:22][CH2:23][CH2:24][CH2:25][N:9]1[C:10]2[C:5](=[CH:4][C:3]([Cl:2])=[C:12]([Cl:13])[CH:11]=2)[N:6]=[CH:7][C:8]1=[O:14])=[O:18])[CH3:21]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 79072Ethyl 2-bromohexanoateHCID 5360545SodiumHCID 144236366,7-Dichloroquinoxalin-2(1H)-one

Produkt 1

HCID 67770344HCID 67770344, VerbindungAusbeute 10,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere sodium (0.148 g, 6.42 mmol) was dissolved in 50 ml of abs. ethanol and 6,7-dichloroquinoxalin-2(1H)-one (1.20 g, 5.58 mmol) (Liebigs Ann. Chem., (1982), 754) was added. The mixture was stirred until the compound dissolved, and ethyl 2-bromohexanoate (1.30 ml, 7.1 mmol) was added. The reaction mixture was refluxed for 72 h, cooled to room temperature, then poured onto crushed ice and acidified by dilute hydrochloric acid (pH=2). The precipitated compound was extracted with ethyl acetate and purified by column chromatography on silica gel (eluent 15% THF in heptane) to afford 0,21 g of 1-((1-ethoxycarbonyl)pentyl)-6,7-dichloroquinoxalin-2(1H)-one 1H-NMR(DMSO-d6):δ 0.78(t, 3H), 1.1(t, 3H), 1.15-1.35(m, 4H), 2.0-2.25(m, 2H), 4.02-4.18(m, 2H), 5.58-5.75(m, 1H), 8.02-8.36(broad, 1H), 8.18(s, 1H), 8.33(s, 1H).

Aufarbeitung

  1. dissolutiondissolved
  2. temperatureThe reaction mixture was refluxed for 72 h
  3. additionpoured
  4. customonto crushed ice
  5. extractionThe precipitated compound was extracted with ethyl acetate
  6. custompurified by column chromatography on silica gel (eluent 15% THF in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-6afe7c461ef34a2fa6c9a9c3277b3e9a
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166155

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