Hydrogen Peroxide → HCID 9818249, Verbindung

HRID 1585574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1585574
[C:1]([N:9]1[C:18]2[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]1[C:20]#[N:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-:23].[Na+].[OH-].[Na+].OO>CC(C)=O.C(OCC)(=O)C>[C:1]([N:9]1[C:18]2[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]1[C:20]([NH2:21])=[O:23])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 784Hydrogen PeroxideHCID 14798Sodium Hydroxide2×HCID 516892Sodium BicarbonateHCID 133367791-Benzoyl-6-chloro-1,2-dihydroquinoline-2-carbonitrile

Produkt 1

HCID 9818249HCID 9818249, VerbindungAusbeute 17,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 1-(Benzoyl)-6-chloro-1,2-dihydro-quinoline-2-carbonitrile (8.0 g), sodium bicarbonate (4.0 g), and 0.1N aqueous sodium hydroxide (20 mL) in acetone (125 mL) was treated with slow addition of 30% hydrogen peroxide (120 mL). The pH of the reaction was kept near 8 by the addition of 0.1N sodium hydroxide. After 4 hours, the mixture was diluted with ethyl acetate and washed with an aqueous solution of sodium thiosulfate. The organic phase was subsequently washed with water and brine. The organic phase was dried over magnesium sulfate and evaporated to dryness. The residue was chromatographed on silica gel using ethyl acetate/hexane (2:8) followed by ethyl acetate/methylene chloride/hexane (3:1:6) and finally 100% ethyl acetate to yield 1.5 g of the desired compound as a white solid, m.p. 230-234° C.

Aufarbeitung

  1. washwashed with an aqueous solution of sodium thiosulfate
  2. washThe organic phase was subsequently washed with water and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4d61af87df2542f0b74f31d4919441e7
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05939435

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