Thionyl Chloride → Methyl 7-(benzyloxy)-4-chloro-6-quinolinecarboxylate

HRID 1433574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433574
S(Cl)([Cl:3])=O.[CH2:5]([O:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17](=O)[CH:18]=[CH:19][NH:20]2)=[CH:15][C:14]=1[C:24]([O:26][CH3:27])=[O:25])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN(C)C=O>[CH2:5]([O:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17]([Cl:3])=[CH:18][CH:19]=[N:20]2)=[CH:15][C:14]=1[C:24]([O:26][CH3:27])=[O:25])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 22936245Methyl 7-(benzyloxy)-4-oxo-1,4-dihydro-6-quinolinecarboxylate

Produkt 1

HCID 22936661Methyl 7-(benzyloxy)-4-chloro-6-quinolinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

After adding thionyl chloride (70 ml) and a catalytic amount of dimethylformamide to methyl 7-(benzyloxy)-4-oxo-1,4-dihydro-6-quinolinecarboxylate (7.19 g, 23.2 mmol), the mixture was heated to reflux for 3 hours while stirring. The reaction solution was concentrated under reduced pressure, a 2N sodium hydroxide solution was gradually added for neutralization, extraction was performed with ethyl acetate, and the organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off, diethyl ether was added for crystallization, and the crystals were filtered out and blow-dried to obtain the title compound (4.067 g, 12.4 mmol) as light brown crystals.

Aufarbeitung

  1. temperatureto reflux for 3 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additiona 2N sodium hydroxide solution was gradually added for neutralization, extraction
  4. washthe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. additiondiethyl ether was added for crystallization
  8. filtrationthe crystals were filtered out and
  9. customblow-dried

Quellen und Nachweise

ORD-Eintrag
ord-5096a1617210436aa8e9a964b81a33a2
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612092B2

Notizen zur Reaktion

Wird geladen…