Methanol → 2-Chloro-4-methoxy-6-methylquinoline

HRID 430086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 430086
[Cl:1][C:2]1[CH:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=1.[OH-:14].[K+].[CH3:16]O>>[Cl:1][C:2]1[CH:11]=[C:10]([O:14][CH3:16])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 27546682,4-Dichloro-6-methylquinoline

Produkt 1

HCID 183537192-Chloro-4-methoxy-6-methylquinoline

Versuchsvorschrift

To 2,4-dichloro-6-methylquinoline (4.1 g, 19 mmol) in methanol (34 ml) was added KOH (1.42 g) and the resulting solution was heated under reflux for 2.5 h. The mixture was concentrated in vacuo and partitioned between ethyl acetate and half-concentrated brine. The organic layer was concentrated and chromatographed (silica gel, EtOAc:hexanes 1:5→1:3). 4-Chloro-2-methoxy-6-methylquinoline eluted first, then 2,4-dichloro-6-methylquinoline, followed by the colourless crystalline title compound, (1.97 g, 49%). δH (CDCl3) 2.52 (s, 3H), 4.05 (s, 3H), 6.71 (s, 1H), 7.53 (dd, J=8.6, 2.0, 1H), 7.83 (d, J=8.6, 1 H), 7.90 (br, s, 1 H); MS (AP+) 208 (MH+, 100%).

Aufarbeitung

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 2.5 h
  3. concentrationThe mixture was concentrated in vacuo
  4. custompartitioned between ethyl acetate and half-concentrated brine
  5. concentrationThe organic layer was concentrated
  6. customchromatographed (silica gel, EtOAc:hexanes 1:5→1:3)
  7. wash4-Chloro-2-methoxy-6-methylquinoline eluted first

Quellen und Nachweise

ORD-Eintrag
ord-e9625519c4b2439a980f784e91b06e6a
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06320051B1

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