Pyridine → Des-(2-cyclohexane-1,3-dione) Fenquinotrione Ethyl Ester

HRID 240355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 240355
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6](=[O:12])[NH:7]2.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](OB(O)O)=[CH:22][CH:21]=1.N1C=CC=CC=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CCCCCC.C(OCC)(=O)C.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6](=[O:12])[N:7]2[C:23]1[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1

Komponenten

9

Edukt 4

HCID 1049PyridineHCID 8471TriethylamineHCID 147699944-Methoxyphenyl boric acidHCID 67531483Ethyl 5-chloro-2-oxo-1,2-dihydroquinoxaline-3-carboxylate

Produkt 1

HCID 67533339Des-(2-cyclohexane-1,3-dione) Fenquinotrione Ethyl EsterAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 8895Cupric acetateKatalysatorHCID 6212ChloroformLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a slurry containing 5.7 g (22.6 mmol) of ethyl 5-chloro-2-oxo-1,2-dihydroquinoxaline-3-carboxylate, 6.9 g (45.4 mmol) of 4-methoxyphenylboric acid, 8.2 g (45.1 mmol) of anhydrous copper (II) acetate and chloroform (200 ml), 3.6 g (45.5 mmol) of pyridine and 4.6 g (45.5 mmol) of triethylamine were added dropwise, and the mixture was stirred for 72 hours at room temperature. The reaction mixture was washed with 10% hydrochloric acid, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was isolated by silica gel chromatography (developing solvent: ethyl acetate:hexane=2:3), and the isolated solid was washed with diisopropyl ether, to obtain 6.3 g (yield: 78%) of ethyl 5-chloro-1-(4-methoxyphenyl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylate as a pale yellow powder.

Aufarbeitung

  1. additionwere added dropwise
  2. washThe reaction mixture was washed with 10% hydrochloric acid
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. washthe isolated solid was washed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-9ae5fae523844b15b5eaaa0a82285c02
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648075B2

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