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Hydrochloric Acid → 3-[1-(1-hydroxy-ethyl)-1H-indol-3-yl]-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione

HRID 427770
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 427770
C[O:2][CH:3]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[C:15](=[O:33])[NH:16][C:17](=[O:32])[C:18]=2[C:19]2[C:27]3[C:22](=[CH:23][C:24]([N+:28]([O-:30])=[O:29])=[CH:25][CH:26]=3)[N:21]([CH3:31])[CH:20]=2)=[CH:6]1)[CH3:4].Cl.CCOC(C)=O>C1COCC1.[Cl-].[Na+].O>[OH:2][CH:3]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[C:15](=[O:33])[NH:16][C:17](=[O:32])[C:18]=2[C:19]2[C:27]3[C:22](=[CH:23][C:24]([N+:28]([O-:30])=[O:29])=[CH:25][CH:26]=3)[N:21]([CH3:31])[CH:20]=2)=[CH:6]1)[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 183577163-[1-(1-methoxy-ethyl)-1H-indol-3-yl]-4-(1-methyl-6nitro-1H-indol-3-yl)-pyrrole-2,5-dione

Produkt 1

HCID 183577193-[1-(1-hydroxy-ethyl)-1H-indol-3-yl]-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dioneAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 3-[l -(1-methoxy-ethyl)-1H-indol-3-yl]-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (3.75 gm) (from step c) above) in 100 mL of THF was added 2 N HCl (75 mL). The solution was stirred at room temperature for 3 hours, and poured into EtOAc and brine. The layers were separated, and the aqueous layer was extracted with EtOAc. The combined EtOAc layers were dried over magnesium sulfate, and evaporated. The residue was purified by flash chromatography using EtOAc/hexanes to give 1.1 gm (Yield 33%) of 3-[1-(1-hydroxy-ethyl)-1H-indol-3-yl]-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione.

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined EtOAc layers were dried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c21cafbde05f4bbf99e57cd8905ed91d
Quelldatensatz
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06313143B1

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