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Hydrochloric Acid → HCID 178424169, Verbindung

HRID 1700530
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1700530
[CH3:1][C:2]1[C:10]2[C:9](=O)[CH2:8][CH:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[CH2:6][C:5]=2[NH:4][CH:3]=1.[C:19]([NH:22][NH2:23])([NH2:21])=[NH:20].[ClH:24].Cl.O>C(O)C>[ClH:24].[NH:22]([N:23]=[C:9]1[CH2:8][CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH2:6][C:5]2[NH:4][CH:3]=[C:2]([CH3:1])[C:10]1=2)[C:19]([NH2:21])=[NH:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 111074403-Methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindol-4-oneHCID 178418668HCID 178418668, Verbindung

Produkt 1

HCID 178424169HCID 178424169, VerbindungAusbeute 4,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

A mixture of 3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindol-4-one (0.70 g), aminoguanidine hydrochloride (0.34 g), concentrated hydrochloric acid (0.44 ml), water (0.44 ml) and ethanol (50 ml) was refluxed for 12 hours. Under reduced pressure, the solvent was evaporated. To the residue was added sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/MeOH/Et3N). The resulting oil was dissolved in ethanol, and to the solution was added 1N hydrochloric acid. The solvent was evaporated, and the residue was recrystallized from ethanol-ethyl acetate to give 4-guanidinoimino-3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindole hydrochloride (Compound 6) (0.04 g) as colorless crystals.

Aufarbeitung

  1. temperaturewas refluxed for 12 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. additionTo the residue was added sodium hydrogen carbonate solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified with silica gel column chromatography (EtOAc/MeOH/Et3N)
  9. dissolutionThe resulting oil was dissolved in ethanol
  10. additionto the solution was added 1N hydrochloric acid
  11. customThe solvent was evaporated
  12. customthe residue was recrystallized from ethanol-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a27b4e8c2a644b26843b70b10eda8be3
Quelldatensatz
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06350749B1

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