Chloroform → Ethyl 4,5,7-trichloro-8-methoxyquinoline-3-carboxylate

HRID 623416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 623416
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:16])=[CH:13][CH:12]=C[C:10]=2[O:17][CH3:18])=[O:5])[CH3:2].S(Cl)([Cl:22])(=O)=O.[CH:24]([Cl:27])(Cl)Cl>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:16])=[C:13]([Cl:22])[CH:12]=[C:24]([Cl:27])[C:10]=2[O:17][CH3:18])=[O:5])[CH3:2]

Komponenten

4

Edukt 3

HCID 6212Chloroform2×HCID 24648Sulfuryl chloride2×HCID 3045573-Quinolinecarboxylic acid, 4-chloro-8-methoxy-, ethyl ester

Produkt 1

HCID 57939336Ethyl 4,5,7-trichloro-8-methoxyquinoline-3-carboxylateAusbeute 29 %

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a stirred solution of 4-chloro-8-methoxy-quinoline-3-carboxylic acid ethyl ester (1.00 g, 3.76 mmol) in chloroform (50 mL) was added, dropwise over 1 h, a solution of sulfuryl chloride (15 mL) in chloroform (15 mL) whilst maintaining the temperature at 25-30° C. The solution was then heated at 60-70° C. for 48 h. During this time, further sulfuryl chloride (2 mL) was added at regular intervals (2, 24 and 30 h). The solution was allowed to cool to RT and added to ice-aqueous ammonia, adjusting the pH to 8. The mixture was then extracted with dichloromethane (20 mL×3), the extracts combined and concentrated. Column chromatography (silica gel, dichloromethane/methanol (100:1)) gave the title compound 26 as a cream solid (0.36 g, 29%). 1H-NMR (CDCl3, 400 MHz): δ 9.04 (s, 1H), 7.78 (s, 1H), 4.51 (q, J=7.1, 2 H), 4.14 (s, 3H), 1.46 (t, J=7.1, 3 H).

Aufarbeitung

  1. temperatureto cool to RT
  2. additionadded to ice-aqueous ammonia
  3. extractionThe mixture was then extracted with dichloromethane (20 mL×3)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2681281dee0f4661a296868bacfedb0d
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09302993B2

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