Sodium Hydroxide → HCID 22643234, Verbindung

HRID 2414755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2414755
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12]C(=O)C)[CH:10]=2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH:3]=1.[OH-].[Na+]>Cl>[CH:22]1([C:19]2[CH:18]=[CH:17][C:16]([C:4]3[CH:3]=[C:2]([NH2:1])[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([NH2:12])[CH:10]=4)[N:5]=3)=[CH:21][CH:20]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 22643183HCID 22643183, Verbindung

Produkt 1

HCID 22643234HCID 22643234, VerbindungAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

N-[4-Amino-2-(4-cyclohexylphenyl)-quinolin-6-yl]-acetamide (22 g) was placed in a 1 L flask to which 500 mL of 6 N HCl was added and the mixture heated with stirring to 95° C. for 18 hrs. After this time, the solution was cooled in ice and was then cautiously neutralized with concentrated NaOH solution, followed by adjustment to pH 9.5. The solution was then poured into a 2 L separatory funnel and extracted with ethyl acetate. The organic layer was then dried over Na2SO4, filtered and concentrated to give 17 g of the desired product. Repeated crystallization using methanol, methylene chloride and hexane provided 9.0 g (41%) of the pure title compound.

Aufarbeitung

  1. additionwas added
  2. temperaturethe mixture heated
  3. temperatureAfter this time, the solution was cooled in ice
  4. additionThe solution was then poured into a 2 L separatory funnel
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was then dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-46a1bce4257349b38391b9a69d214e9d
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06815447B2

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