Dimethyl acetylenedicarboxylate → 2-(Methoxycarbonyl)-4-oxo-6,8-dichloro-7-methylquinoline

HRID 6678

Reaktionsgleichung

Reaktionsgleichung von HRID 6678
[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH3:10].[C:11]([C:17](OC)=[O:18])#[C:12][C:13]([O:15][CH3:16])=[O:14]>CO>[CH3:16][O:15][C:13]([C:12]1[CH2:11][C:17](=[O:18])[C:6]2[C:7](=[C:2]([Cl:1])[C:3]([CH3:10])=[C:4]([Cl:9])[CH:5]=2)[N:8]=1)=[O:14]

Komponenten

4

Edukt 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 882822,4-Dichloro-m-toluidine

Produkt 1

HCID 684344222-(Methoxycarbonyl)-4-oxo-6,8-dichloro-7-methylquinolineAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2,6-dichloro-3-aminotoluene (20.5 g, 0.11 mol) in methanol (300 mL) was added dimethyl acetylenedicarboxylate (15 mL, 0.12 mol) and the reaction mixture was refluxed for 2 hours. The reaction mixture was concentrated under reduced pressure to a yellow solid. Diphenyl ether (350 mL) was heated to 230–240° C., and the yellow solid was added to it. The temperature was maintained at 230–240° C. for 20 minutes and the reaction mixture was cooled slowly to ambient temperature and diluted with petroleum ether (1L). The solid was filtered and washed with hot ethyl acetate to afford a brown solid, 2-(methoxycarbonyl)-4-oxo-6,8-dichloro-7-methylquinoline (28.5 g, 85%); NMR (CDCl3) 2.62 (s, 3), 4.04 (s, 3), 7.02 (s, 1), 8.24 (s, 1) ppm.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure to a yellow solid
  3. temperatureDiphenyl ether (350 mL) was heated to 230–240° C.
  4. additionthe yellow solid was added to it
  5. temperatureThe temperature was maintained at 230–240° C. for 20 minutes
  6. additiondiluted with petroleum ether (1L)
  7. filtrationThe solid was filtered
  8. washwashed with hot ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4b5891dc96b04f91a5dc14cb3e9eaccd
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084142B2

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