Water → 3-(3-Chloro-6-fluoro-3,4-dihydroquinolin-2-on-7-yl)-1-methyl-6-trifluoromethyluracil

HRID 1033160Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1033160
[Cl:1][CH:2]([CH2:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[C:16]2=[O:27])=[CH:10][C:9]=1[N+:28]([O-])=O)[C:3]([O:5]C)=O.O>C(O)(=O)C.[Fe]>[Cl:1][CH:2]1[CH2:7][C:8]2[C:9](=[CH:10][C:11]([N:15]3[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[C:16]3=[O:27])=[C:12]([F:14])[CH:13]=2)[NH:28][C:3]1=[O:5]

Komponenten

5

Edukt 2

HCID 962WaterHCID 19025375methyl 2-chloro-3-[5-fluoro-2-nitro-4-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)phenyl]propanoate

Produkt 1

HCID 190253833-(3-Chloro-6-fluoro-3,4-dihydroquinolin-2-on-7-yl)-1-methyl-6-trifluoromethyluracilAusbeute 221,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

This compound was prepared in a manner analogous to that of Step D of this Example, using 2.9 grams (0.006 mole) of methyl 2-chloro-3-[5-fluoro-2-nitro-4-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)phenyl]propanoate, 2.0 grams (0.036 g-atom) of iron powder, and 5 mL of water in 50 mL of acetic acid. The product from this reaction was combined with that from another run (0.014 mole) of this reaction. The combination was subjected to column chromatography on silica gel. Elution was accomplished using heptane, 1:1 heptane-ethyl acetate, and ethyl acetate. The product-containing fractions were combined and concentrated under reduced pressure, yielding 5.2 grams of 3-(3-chloro-6-fluoro-3,4-dihydroquinolin-2-on-7-yl)-1-methyl-6-trifluoromethyluracil. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. customThis compound was prepared in a manner analogous to that of Step D of this Example
  2. customfrom another run (0.014 mole) of this reaction
  3. washElution
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-79346ff66d8c465b86a676bbb2e69355
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05310723

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