Acetic Acid → 1-(1H-indol-3-yl)ethanamine

HRID 2247595Notes

Reaction equation

HRID 2247595 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[N:12]O)[CH3:11])=[CH:2]1.C(O)(=O)C.[H][H]>C(O)C.[C].[Pd]>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]([NH2:12])[CH3:11])=[CH:2]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 30141241-(1H-indol-3-yl)ethanone oximeHCID 178418361HCID 178418361, compound

Product 1

HCID 30157011-(1H-indol-3-yl)ethanamineYield 74.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

10% palladium-carbon (water content: 50%, 12.2 mg) was added to a solution of 1-(1H-indol-3-yl)ethanone oxime (0.20 g) obtained as above and acetic acid (0.7 mL) in ethanol (7 mL) at room temperature. The reaction mixture was stirred in a hydrogen stream at room temperature for 10 hours, and then filtered on a celite. The filtrate was concentrated under reduced pressure. The residue was extracted with chloroform. The organic layer was washed sequentially with a 1 N aqueous solution of sodium hydroxide and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Carrier: Chromatorex™ NH, elution solvent: chloroform-methanol system) to obtain 0.137 g of the title compound.

Workup

  1. filtrationfiltered on a celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. extractionThe residue was extracted with chloroform
  4. washThe organic layer was washed sequentially with a 1 N aqueous solution of sodium hydroxide and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (Carrier: Chromatorex™ NH, elution solvent: chloroform-methanol system)

Sources & evidence

ORD record
ord-c6dd8cdac9c548c7818338ccd7d74180
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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