Sodium Hydroxide → (5-Methyl-1H-imidazol-4-yl)(quinolin-7-yl)methanone

HRID 1643391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1643391
[CH3:1][C:2]1[N:3]=[CH:4][N:5](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:6]=1[C:7]([C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)=[O:8].[OH-].[Na+]>C(O)(=O)C.O>[CH3:1][C:2]1[NH:3][CH:4]=[N:5][C:6]=1[C:7]([C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)=[O:8]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 66755765HCID 66755765, Verbindung

Produkt 1

HCID 57965246(5-Methyl-1H-imidazol-4-yl)(quinolin-7-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899381Acetic acid--water (1/1)Lösungsmittel

Versuchsvorschrift

A solution of (8) in acetic acid/water (12 mL/8 mL) was heated at 110° C. for 1.5 h. The reaction was cooled to room temperature. Crushed ice was added, and basification of reaction with NaOH (s) to pH˜6 was followed. The aqueous layer was extracted with chloroform/isopropanol (3:1, 200 mL). The pooled organic layers were dried over magnesium sulfate. The mixture was filtered, and the solvents were removed under vacuum. The residue was purified by chromatography on silica gel with 3% saturated ammonia methanol in dichloromethane to give (5-methyl-1H-imidazol-4-yl)(quinolin-7-yl)methanone (9) as a white solid (0.53 g, 2.24 mmol, 35% over 3 steps).

Aufarbeitung

  1. additionCrushed ice was added
  2. extractionThe aqueous layer was extracted with chloroform/isopropanol (3:1, 200 mL)
  3. dry with materialThe pooled organic layers were dried over magnesium sulfate
  4. filtrationThe mixture was filtered
  5. customthe solvents were removed under vacuum
  6. customThe residue was purified by chromatography on silica gel with 3% saturated ammonia methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-cbae4f6faf7543488887f88093e5c72d
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119807B2

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