Ethanolamine → HCID 67339071, compound

HRID 1725359Notes

Reaction equation

HRID 1725359 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]=O)[CH:10]=1)[NH:7][CH:6]=[CH:5]2.[NH2:13][CH2:14][CH2:15][OH:16].[H][H]>CO.[Pd]>[OH:16][CH2:15][CH2:14][NH:13][CH2:11][C:9]1[CH:10]=[C:2]([CH3:1])[CH:3]=[C:4]2[C:8]=1[NH:7][CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 700EthanolamineHCID 17985409HCID 17985409, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67339071HCID 67339071, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dissolve 5-Methyl-1H-indole-7-carboxaldehyde (4.036 g, 25.384 mmol) in absolute methanol (200 mL), add 2-aminoethanol (3.1 g, 50.767 mmol) and 10% palladium on carbon (0.4 g). Stir the mixture for 1 hour under nitrogen, then under 1 atmosphere of hydrogen for 3 hours. Filter, concentrate under reduced pressure, and purify by flash column chromatography (silica gel, 90/19/1, dichloromethane/methanol/ammonia) to give the title compound as a colorless oil.

Workup

  1. filtrationFilter
  2. concentrationconcentrate under reduced pressure
  3. custompurify by flash column chromatography (silica gel, 90/19/1, dichloromethane/methanol/ammonia)

Sources & evidence

ORD record
ord-47adc58355d34385939ca2d55e9a403f
Source dataset
uspto-grants-2009_02
Patent number
US07491716B2

Reaction notes

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