Hydrochloric Acid → 7-((5-Methyl-1H-imidazol-4-yl)methyl)quinoline
Reaktionsgleichung
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=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.[OH-].[K+].O.NN.Cl>C(O)CO>[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
A mixture of (9) (0.53 g, 2.23 mmol), potassium hydroxide (0.50 g, 8.91 mol), and hydrazine hydrate (0.45 mL, 14.4 mmol) in ethylene glycol was heated at 120° C. for 1 h, then kept at 165° C. overnight. The reaction mixture was cooled to room temperature and acidified with 2 M HCl (aq) to pH˜4. The aqueous layer was washed with chloroform/isoprpanol (3:1, 200 ml). The aqueous layer was basified to pH˜7, and 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 7-((5-methyl-1H-imidazol-4-yl)methyl)quinoline (10) as a yellow foam (0.32 mg, 1.45 mmol, 65% yield).
Aufarbeitung
- temperatureThe reaction mixture was cooled to room temperature
- washThe aqueous layer was washed with chloroform/isoprpanol (3:1, 200 ml)
- extractionextracted with chloroform/isopropanol (3:1, 200 mL)
- dry with materialThe pooled organic layers were dried over magnesium sulfate
- filtrationThe mixture was filtered
- customthe solvents were removed under vacuum
- customThe residue was purified by chromatography on silica gel with 3% saturated ammonia methanol in dichloromethane
Quellen und Nachweise
- ORD-Eintrag
- ord-2ac26afc246141d1a8f6e1cad364c62e
- Quelldatensatz
- uspto-grants-2012_02
- Patentnummer
- US08119807B2
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