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Ethyl bromoacetate → Ethyl[(9-amino-1,2,3,4-tetrahydroacridin-8-yl)oxy]acetate

HRID 981921
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 981921
Cl.[OH:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:16]=1[C:15]([NH2:17])=[C:14]1[C:9]([CH2:10][CH2:11][CH2:12][CH2:13]1)=[N:8]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(OCC)(=O)C>CN(C)C=O.O>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:16]=1[C:15]([NH2:17])=[C:14]1[C:9]([CH2:10][CH2:11][CH2:12][CH2:13]1)=[N:8]2)[CH3:30]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 136404540HCID 136404540, Verbindung

Produkt 1

HCID 20068607Ethyl[(9-amino-1,2,3,4-tetrahydroacridin-8-yl)oxy]acetateAusbeute 72,91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

8-Hydroxy-1,2,3,4-tetrahydro-9-acridinamine hydrochloride (18.07 g) was suspended in 500 ml of dry dimethylformamide. Potassium carbonate (22.6 g) was added, and the reaction mixture was stirred vigorously for 30 mins. Ethyl bromoacetate (18.0 g) was added dropwise, and the reaction was stirred vigorously overnight. The reaction mixture was distributed between ethyl acetate and water, and the organic layer was separated. The aqueous phase was extracted three times with ethyl acetate, and the combined organic phase was washed with water, dried, filtered, and the filtrate evaporate. The residue was purified by flash chromatography (ethyl acetate, then 5% triethylamine/ethyl acetate) to give 15.75 g (72.91%) of product, mp 141°-142° C.

Aufarbeitung

  1. stirringthe reaction was stirred vigorously overnight
  2. customthe organic layer was separated
  3. extractionThe aqueous phase was extracted three times with ethyl acetate
  4. washthe combined organic phase was washed with water
  5. customdried
  6. filtrationfiltered
  7. customthe filtrate evaporate
  8. customThe residue was purified by flash chromatography (ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-61a0c16f2c874c5eb86c97a86e18353c
Quelldatensatz
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04994452

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