Ethyl Acetate → 2-(6-fluoro-1H-indol-3-yl)ethanamine

HRID 1670735Notes

Reaction equation

HRID 1670735 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[F:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12](/[CH:17]=[CH:18]/[N+:19]([O-])=O)=[CH:13][NH:14]2)=[CH:10][CH:9]=1.C(OCC)(=O)C>O1CCCC1>[F:7][C:8]1[CH:16]=[C:15]2[C:11](=[CH:10][CH:9]=1)[C:12]([CH2:17][CH2:18][NH2:19])=[CH:13][NH:14]2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydride2×HCID 23149935HCID 23149935, compound

Product 1

HCID 8540242-(6-fluoro-1H-indol-3-yl)ethanamineYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

Aluminum lithium hydride (1.36 g) was suspended in tetrahydrofuran (72 ml), 6-fluoro-3-[(E)-2-nitrovinyl]-1H-indole (1.48 g) was dissolved in tetrahydrofuran (20 ml) and added dropwise under ice-cooling, and the mixture was stirred at 60° C. for 1 hr. Under ice-cooling, excess aluminum lithium hydride was decomposed with ice water, ethyl acetate was added, and the mixture was filtered through a celite (trademark) filter. A 1N aqueous sodium hydroxide solution was added to the filtrate, pH was adjusted to not less than 11, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give a brown oil. The oil was purified by amine coating silica gel column chromatography (elution solvent:ethyl acetate-ethyl acetate-methanol (10:1)) to give 6-fluorotryptamine (1.24 g, yield 97%).

Workup

  1. additionadded dropwise under ice-
  2. temperaturecooling
  3. temperatureUnder ice-cooling
  4. additionwas added
  5. filtrationthe mixture was filtered through a celite (trademark)
  6. filtrationfilter
  7. additionA 1N aqueous sodium hydroxide solution was added to the filtrate, pH
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customto give a brown oil
  13. customThe oil was purified by amine coating silica gel column chromatography (elution solvent:ethyl acetate-ethyl acetate-methanol (10:1))

Sources & evidence

ORD record
ord-a84ee850d3264179944487ad967569ad
Source dataset
uspto-grants-2011_08
Patent number
US07994196B2

Reaction notes

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