m-Chloroperbenzoic acid → 7-(2,5-Dichlorothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one-1-oxide

HRID 1700691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1700691
[Cl:1][C:2]1[S:3][C:4]([Cl:19])=[CH:5][C:6]=1[CH:7]1[CH2:16][C:15]2[N:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=2[C:9](=[O:18])[CH2:8]1.ClC1C=CC=C(C(OO)=[O:28])C=1.C(=O)([O-])O.[Na+].N([O-])=O.[Na+]>C1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[S:3][C:4]([Cl:19])=[CH:5][C:6]=1[CH:7]1[CH2:16][C:15]2[N+:14]([O-:28])=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=2[C:9](=[O:18])[CH2:8]1

Komponenten

7

Edukt 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 183173437-(2,5-Dichlorothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneHCID 23668193Sodium Nitrite

Produkt 1

HCID 183177197-(2,5-Dichlorothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one-1-oxideAusbeute 90,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In benzene (15 ml) was dissolved 7-(2,5-dichlorothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (1.09 g), and to the solution was added m-chloroperbenzoic acid (0.963 g). The mixture was stirred at room temperature for 1 hour, and to the mixture were added ethyl acetate (150 ml), saturated sodium hydrogen carbonate solution (200 ml) and sodium nitrite(200 mg). The mixture was shaken, and the separated upper layer was washed with water and concentrated under reduced pressure. The residue was washed with a mixture of isopropylether and ethyl acetate (2:1) to give 7-(2,5-dichlorothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one-1-oxide (1.04 g) as yellow crystals.

Aufarbeitung

  1. stirringThe mixture was shaken
  2. washthe separated upper layer was washed with water
  3. concentrationconcentrated under reduced pressure
  4. washThe residue was washed with a mixture of isopropylether and ethyl acetate (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-8a9743fb78a1493c8862853f0f5d5963
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06350749B1

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