Hydrochloric Acid → 5-Cyanotryptamine

HRID 1666798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666798
Cl.[N+:2]([CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=2)[NH:9][CH:8]=1)([O-])=O.[OH-].[Na+]>CO.[Zn]>[C:16]([C:13]1[CH:14]=[C:15]2[C:10]([NH:9][CH:8]=[C:7]2[CH2:6][CH2:5][NH2:2])=[CH:11][CH:12]=1)#[N:17]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21071455HCID 21071455, Verbindung

Produkt 1

HCID 589265-Cyanotryptamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Add zinc powder (16.22 g, 248.1 mmol) in four portions to 2N HCl (300.0 ml). Add dropwise 3-(2-nitroethyl)-5-cyano-1H-indole (2.25 g, 10.5 mmol) as a solution in methanol (300.0 ml). Heat to reflux. After 2.5 hours, cool to ambient temperature and adjust the pH to 11 using 5N NaOH, filter through Celite, wash with water, then extract the filtrate with dichloromethane. Combine the organic extracts, wash with brine, dry (Na2SO4), then evaporated to give the title compound: mp 102-105° C., MS (ACPI): m/e 186.1 (M+1). Analysis for C11H11N3: Calcd: C, 71.33; H, 5.99; N, 22.69. found: C, 71.03; H, 5.91; N, 22.64.

Aufarbeitung

  1. temperatureHeat to reflux
  2. filtrationfilter through Celite
  3. washwash with water
  4. extractionextract the filtrate with dichloromethane
  5. washwash with brine
  6. dry with materialdry (Na2SO4)
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-5c88f5d917d64303bcf42cee0e337f7b
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044090B2

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