8-Hydroxy-2-quinolinecarboxaldehyde → HCID 178515865, Verbindung

HRID 872224

Reaktionsgleichung

Reaktionsgleichung von HRID 872224
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[C:23]([CH:26]=O)[CH:22]=[CH:21]2.[NH2:28][CH2:29][CH2:30][C:31]1[N:35]=[CH:34][NH:33][CH:32]=1>ClC(Cl)C>[NH:33]1[CH:32]=[C:31]([CH2:30][CH2:29][NH:28][CH2:26][C:23]2[CH:22]=[CH:21][C:20]3[C:25](=[C:16]([OH:15])[CH:17]=[CH:18][CH:19]=3)[N:24]=2)[N:35]=[CH:34]1

Komponenten

5

Edukt 3

HCID 5993428-Hydroxy-2-quinolinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178419017HCID 178419017, Verbindung

Produkt 1

HCID 178515865HCID 178515865, VerbindungAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

Sodium triacetoxyborohydride (225 mg, 1.061 mmol) was added to a stirred solution of 8-hydroxy-quinoline-2-carboxaldehyde 4 (200 mg, 1.156 mmol) and histamine (128 mg, 1.152 mmol) in dichloroethane (10 mL). The mixture was left to stir at RT for 16 h, neutralized (aqueous NaHCO3), and concentrated. The resulting residue, after column chromatography on silica (ethyl acetate/i-PrOH/2 N NH4OH, 6:2:1), afforded 2-{[2-(1H-imidazol-4-yl)-ethylamino]-methyl}-quinolin-8-ol F1 as a straw-colored solid (190 mg, 61%). The above method was repeated using other amines: 2-(aminomethyl)pyridine gave F2 and 2-(2-methylaminoethyl)pyridine gave F3, data given in Table 2.

Aufarbeitung

  1. waitThe mixture was left
  2. concentrationneutralized (aqueous NaHCO3), and concentrated

Quellen und Nachweise

ORD-Eintrag
ord-4ffeafa25e5f4fcb849c1e6e7e83e619
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975278B2

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