Hydrochloric Acid → 5-Cyanotryptamine

HRID 1371856Notes

Reaction equation

HRID 1371856 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

HCID 589265-Cyanotryptamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-45470ed625144098bf7fb8f035852be0
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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