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Hydrochloric Acid → 2-(4-Aminophenyl)-1-benzofuran-5-amine

HRID 1034558
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1034558
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:13]=3[CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.Cl.O1CCOCC1>[Fe].O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:13]=3[CH:14]=2)=[CH:6][CH:5]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 128136015-Nitro-2-(4-nitrophenyl)-1-benzofuran

Produkt 1

HCID 111069902-(4-Aminophenyl)-1-benzofuran-5-amineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysator
HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Then, 12.42 g (1.0 equivalent) of the obtained 2-(p-nitrophenyl)-5-nitrobenzofurane was added to 48.85 g (20.0 equivalents) of a 100 mesh iron powder previously activated by 0.5 ml of concentrated hydrochloric acid in 150 ml of a mixed solvent of 1,4-dioxane and water in proportions of 1:1, and the resulting mixture was refluxed by heating at about 110° C. for 2 hours and heavily stirred. The hot supernatant was filtered with Celite immediately after confirming a completion of the reaction by TLC (Thin-Layer Chromatography). The residual material was adequately washed with hot 1,4-dioxane and filtered. This operation was repeated three or four times, and then filtrates were combined and concentrated by an evaporator. After concentration, recrystallization was carried out with ethanol to obtain 7.1 g of orange-colored 2-(p-aminophenyl)-5-aminobenzofurane (amino compound A) at an yield of 90%.

Aufarbeitung

  1. temperaturethe resulting mixture was refluxed
  2. filtrationThe hot supernatant was filtered with Celite immediately
  3. customa completion of the reaction by TLC (Thin-Layer Chromatography)
  4. washThe residual material was adequately washed with hot 1,4-dioxane
  5. filtrationfiltered
  6. concentrationconcentrated by an evaporator
  7. concentrationAfter concentration, recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-aeec9057008e49d596a500e417dd3173
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08546049B2

Notizen zur Reaktion

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