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Trifluoroacetic acid → Ethyl 7-[4-(aminomethyl)benzyloxy]-4-chloro-1-methyl-2-indolecarboxylate

HRID 1067844
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1067844
C(OC([NH:8][CH2:9][C:10]1[CH:33]=[CH:32][C:13]([CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([Cl:31])=[C:20]3[C:24]=2[N:23]([CH3:25])[C:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:21]3)=[CH:12][CH:11]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][CH2:9][C:10]1[CH:33]=[CH:32][C:13]([CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([Cl:31])=[C:20]3[C:24]=2[N:23]([CH3:25])[C:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:21]3)=[CH:12][CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 21194287HCID 21194287, Verbindung

Produkt 1

HCID 21194237Ethyl 7-[4-(aminomethyl)benzyloxy]-4-chloro-1-methyl-2-indolecarboxylateAusbeute 101,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 0.75 g (1.59 mmol) of ethyl 7-[4-(tert-butoxycarbonylaminomethyl)benzyloxy]-4-chloro-1-methyl-2-indolecarboxylate, 5 ml of trifluoroacetic acid and 50 ml of dichloromethane was stirred at 0° C. for 2 hours. The reaction mixture was concentrated under reduced pressure. Thereafter ice water was poured onto the resulting residue and 28% aqueous ammonia was added thereto to render alkaline (pH=9 to 10). The mixture was then extracted three times with ethyl acetate. The combined extracts were washed with saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 0.60 g (>99%) of ethyl 7-[4-(aminomethyl)benzyloxy]-4-chloro-1-methyl-2-indolecarboxylate.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThereafter ice water was poured onto the resulting residue and 28% aqueous ammonia
  3. additionwas added
  4. extractionThe mixture was then extracted three times with ethyl acetate
  5. washThe combined extracts were washed with saturated sodium chloride solution
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0141accf92ce4ba983e03f2f686fb7cf
Quelldatensatz
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06248772B1

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