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

HRID 1010308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010308
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-c3a0bacc4f5546d29c89a4d577685599
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973160B2

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