Hydrochloric Acid → 5-Cyanotryptamine

HRID 1666798Notes

Reaction equation

HRID 1666798 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-5c88f5d917d64303bcf42cee0e337f7b
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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