Ammonium Chloride → 9-(((3-(Trifluoromethyl)phenyl)methyl)imino)-1,2,3,4,9,10-hexahydroacridin-1-ol

HRID 2309478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2309478
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl-].[NH4+].[F:9][C:10]([F:35])([F:34])[C:11]1[CH:12]=[C:13]([CH:31]=[CH:32][CH:33]=1)[CH2:14][NH:15][C:16]1[C:17]2[C:22]([N:23]=[C:24]3[C:29]=1[C:28](=[O:30])[CH2:27][CH2:26][CH2:25]3)=[CH:21][CH:20]=[CH:19][CH:18]=2>C1COCC1>[F:34][C:10]([F:9])([F:35])[C:11]1[CH:12]=[C:13]([CH:31]=[CH:32][CH:33]=1)[CH2:14][NH:15][C:16]1[C:17]2[C:22]([N:23]=[C:24]3[C:29]=1[CH:28]([OH:30])[CH2:27][CH2:26][CH2:25]3)=[CH:21][CH:20]=[CH:19][CH:18]=2

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 13935142HCID 13935142, VerbindungHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 30256269-(((3-(Trifluoromethyl)phenyl)methyl)imino)-1,2,3,4,9,10-hexahydroacridin-1-olAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

In 100 ml dry THF was dissolved in 3.86 g of 3,4-dihydro-9-(3-trifluoromethylbenzyl)aminoacridin-1(2H)-one. The solution was stirred mechanically under nitrogen and cooled in ice. To it was added 5.2 ml of 1M LiAlH4 in THF dropwise. After stirring an additional 0.5 hour, the reaction was complete. It was neutralized with 1 ml of saturated ammonium chloride and the salts were filtered off. The THF filtrate was evaporated to an oil which solidified upon trituration with pentane. The solid was recrystallized from 1:1 dichloromethane/pentane to yield 3.12 g of solid, mp 154°-155° C.

Aufarbeitung

  1. temperaturecooled in ice
  2. stirringAfter stirring an additional 0.5 hour
  3. filtrationthe salts were filtered off
  4. customThe THF filtrate was evaporated to an oil which
  5. customThe solid was recrystallized from 1:1 dichloromethane/pentane

Quellen und Nachweise

ORD-Eintrag
ord-bc5eeb6e24244288bf4021761945cf89
Quelldatensatz
uspto-grants-1987_09
Patentnummer
US04695573

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