Ammonium Chloride → (4-Benzyloxy-benzyl)-quinolin-6-yl-amine

HRID 2080260Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2080260
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:33]=[CH:32][C:18]([C:19]([NH:21][C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]=[CH:27][CH:26]=[CH:25]3)=O)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N1C=CC=CC=1OCC1C=CC(CNC(C2C(N)=NC(N)=CN=2)=O)=CC=1.[Cl-].[NH4+]>O1CCCC1>[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][NH:21][C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]=[CH:27][CH:26]=[CH:25]3)=[CH:32][CH:33]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 23130518HCID 23130518, VerbindungHCID 58875320HCID 58875320, Verbindung

Produkt 1

HCID 58875328(4-Benzyloxy-benzyl)-quinolin-6-yl-amineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of lithium aluminum hydride (58 mg, 1.54 mmol) in tetrahydrofuran (10 mL) was added a solution of 4-benzyloxy-N-quinolin-6-yl-benzamide described in Preparation Example Z+-3 (218 mg, 0.615 mmol) in tetrahydrofuran (1 mL), and the solution was stirred under reflux for 7 hours. The reaction solution was allowed to room temperature, an aqueous solution of saturated ammonium chloride was added, the solution was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by NH silica gel column chromatography (hexane: ethyl acetate), and the title compound (147 mg, 70%) was obtained as a yellow solid.

Aufarbeitung

  1. temperatureunder reflux for 7 hours
  2. customwas allowed to room temperature
  3. extractionthe solution was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by NH silica gel column chromatography (hexane: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d85b9663ac114467940b276b0cbad6e6
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932272B2

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