Ammonia → Ethyl acetate hexane

HRID 443032

Reaktionsgleichung

Reaktionsgleichung von HRID 443032
[OH:1][C:2]1[C:15]2[C:6](=CC3C(N=2)=CC=CC=3)[CH:5]=[CH:4][CH:3]=1.Cl.NC1C=CC(N(CC)CC)=CC=1C.[CH2:30]([OH:32])[CH3:31].N>O.[N+]([O-])([O-])=O.[Ag+]>[CH3:6][CH2:15][CH2:2][CH2:3][CH2:4][CH3:5].[C:30]([O:1][CH2:2][CH3:15])(=[O:32])[CH3:31]

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 702EthanolHCID 874624-HydroxyacridineHCID 108623N,N-Diethyltoluene-2,5-diamine hydrochloride

Produkt 1

HCID 21226206Ethyl acetate hexaneAusbeute 19,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24470Silver NitrateKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

While stirring a mixture comprising 195 mg of 4-hydroxyacridine (20), 214 mg of 2-amino-5-diethylaminotoluene hydrochloride (21) and 6.8 ml of ethanol at 20° C., a solution comprising 0.17 mg of silver nitrate dissolved in 0.75 ml of water was added thereto drop-by-drop. Next, with 0.85 ml of 25% ammonia solution added to the mixture, reaction was allowed to proceed at 20° C. for a period of 24 hr. After the completion of the reaction, the reacted solution was introduced into water. After extraction by ethyl acetate, the extract was concentrated. After purification by column chromatography, 72.5 mg of indoaniline derivative (25) described in the exemplified compound 4-1 was obtained as deep blue crystals on recrystallization by hexane-ethyl acetate (yield 19.6%).

Aufarbeitung

  1. additionwas added
  2. customAfter the completion of the reaction
  3. extractionAfter extraction by ethyl acetate
  4. concentrationthe extract was concentrated
  5. customAfter purification by column chromatography, 72.5 mg of indoaniline derivative (25)

Quellen und Nachweise

ORD-Eintrag
ord-4a3944fdc39c4cfa8eadcfe049da78b7
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05892042

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