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Ammonium Chloride → 1-Acridinol, 1,2,3,4-tetrahydro-9-((2-phenylethyl)amino)-, (Z)-2-butenedioate (1:1) (salt)

HRID 1763018
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1763018
[CH2:1]([NH:9][C:10]1[C:11]2[C:16]([N:17]=[C:18]3[C:23]=1[C:22](=[O:24])[CH2:21][CH2:20][CH2:19]3)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-].[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37]>O1CCCC1.CCOCC.C(O)(C)C>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37].[CH2:1]([NH:9][C:10]1[C:11]2[C:16]([N:17]=[C:18]3[C:23]=1[CH:22]([OH:24])[CH2:21][CH2:20][CH2:19]3)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 25517Ammonium ChlorideHCID 444266Maleic AcidHCID 13756055HCID 13756055, VerbindungHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 137560631-Acridinol, 1,2,3,4-tetrahydro-9-((2-phenylethyl)amino)-, (Z)-2-butenedioate (1:1) (salt)Ausbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittel
HCID 3776IsopropanolLösungsmittel2×
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In 75ml of dry tetrahydrofuran was dissolved 2.45 g of 9-phenethylamino-3,4-dihydroacridin-1(2H)-one. The solution was cooled in ice and 7.0ml (1 eq) of 1.1 M LiAlH4 in Et2O was added dropwise. After 0.5 hour the reaction was complete. It was neutralized with 0.5ml saturated NH4Cl solution and the resulting inorganic salts were filtered off. The filterate was evaporated to a solid and the maleate salt was found by adding a solution of 1.1 eq maleic acid in isopropanol to a suspension of the product in isopropanol. A solution formed initially but the salt precipitated out over 0.5 hour at ambient temperatures. The salt was filtered off and recrystallized from 5:1 EtOAc/MeOH and dried at 80° C. in vacuo to yield 1.14 g (32%) of a solid, melting point 169° C.

Aufarbeitung

  1. temperatureThe solution was cooled in ice
  2. filtrationthe resulting inorganic salts were filtered off
  3. customThe filterate was evaporated to a solid
  4. customA solution formed initially
  5. customthe salt precipitated out over 0.5 hour at ambient temperatures
  6. filtrationThe salt was filtered off
  7. customrecrystallized from 5:1 EtOAc/MeOH
  8. customdried at 80° C. in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bd57e02bb2a540bdaa75dd4cc28ac036
Quelldatensatz
uspto-grants-1989_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04835275

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