Sodium Hydroxide → 4-Chloro-6-methylquinoline

HRID 651639

Reaktionsgleichung

Reaktionsgleichung von HRID 651639
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6][C:5]2=O.[OH-].[Na+].P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH3:1])[CH:3]=2)[N:8]=[CH:7][CH:6]=1

Komponenten

4

Edukt 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 2560804-Hydroxy-6-methylquinoline

Produkt 1

HCID 8246244-Chloro-6-methylquinoline

Versuchsvorschrift

6-Methyl-(1H)-quinolin-4-one (1.57 g, 9.7 mmol) in 20 mL phosphorus oxychloride is heated to 110° C. for 4 hours. The mixture is cooled to room temperature then diluted with ice water (˜200 mL) and the pH is adjusted to ca. 10 by the slow addition of 10 N NaOH. The aqueous solution is extracted with methylene chloride (4×250 mL) and the combined organic layers washed with brine, dried over Na2SO4, filtered and concentrated. The crude residue is filtered through silica gel with 33% EtOAc/hexanes to give the product (1.05 g, 5.9 mmol) as a yellow solid.

Aufarbeitung

  1. extractionThe aqueous solution is extracted with methylene chloride (4×250 mL)
  2. washthe combined organic layers washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. filtrationThe crude residue is filtered through silica gel with 33% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c35d37b3df28424b871f1e136ee38036
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06281227B1

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