Ammonium Chloride → 1-Acridinol, 1,2,3,4-tetrahydro-9-(((3-fluorophenyl)methyl)amino)-

HRID 580733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 580733
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][NH:6][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:20]=1[C:19](=[O:21])[CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][NH:6][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:20]=1[CH:19]([OH:21])[CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 13935131HCID 13935131, VerbindungHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 30256191-Acridinol, 1,2,3,4-tetrahydro-9-(((3-fluorophenyl)methyl)amino)-Ausbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

In 100 ml of THF was dissolved 3.00 g of 3,4-dihydro-9-(3-fluorobenzylamino)acridin-1(2H)-one. The mechanically stirred solution was cooled in ice under nitrogen and 4.68 ml of 1M lithium aluminum hydride in THF was added dropwise over 15 minutes. After 0.5 hour, analysis by TLC indicated the reaction was complete, so it was neutralized with 1 ml of saturated ammonium chloride solution and the resulting salts were filtered. The filtrate was evaporated to an oil which crystallized on trituration with pentane. The solid was filtered and recrystallized from 1:1 dichloromethane/pentane to yield 2.50 g of solid, mp 128° C.

Aufarbeitung

  1. temperatureThe mechanically stirred solution was cooled in ice under nitrogen
  2. filtrationthe resulting salts were filtered
  3. customThe filtrate was evaporated to an oil which
  4. customcrystallized on trituration with pentane
  5. filtrationThe solid was filtered
  6. customrecrystallized from 1:1 dichloromethane/pentane

Quellen und Nachweise

ORD-Eintrag
ord-cf8bfb2155d3420bb629d18903abd0c2
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04754050

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